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Boston Post Road
Boston Post Road
from Wikipedia

Boston Post Road
Routes of the Boston Post Road
Major junctions
South end US 1 in New York City
North end Route 1A in Boston
Location
CountryUnited States
Highway system

The Boston Post Road was a system of mail-delivery routes between New York City and Boston, Massachusetts, that evolved into one of the first major highways in the United States.

The three major alignments were the Lower Post Road (now U.S. Route 1 (US 1) along the shore via Providence, Rhode Island), the Upper Post Road (now US 5 and US 20 from New Haven, Connecticut, by way of Springfield, Massachusetts), and the Middle Post Road (which diverged from the Upper Road in Hartford, Connecticut, and ran northeastward to Boston via Pomfret, Connecticut).

In some towns, the area near the Boston Post Road has been placed on the National Register of Historic Places, since it was often the first road in the area, and some buildings of historical significance were built along it. The Boston Post Road Historic District, including part of the road in Rye, New York, has been designated a National Historic Landmark. The Post Road is also famous for milestones that date from the 18th century, many of which survive to this day. In parts of Connecticut (generally east of Hartford), it is also known as Route 6.

History

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The Upper Post Road was originally called the Pequot Path and had been in use by Native Americans long before Europeans arrived.[1] Some of these important native trails were in many places as narrow as two feet.[2]

What is now called the Old Connecticut Path and the Bay Path were used by John Winthrop the Younger to travel from Boston to Springfield in November 1645, and these form much of the basis for the Upper Post Road.

The colonists first used this trail to deliver the mail using post riders. The first ride to lay out the Upper Post Road started on January 1, 1673.[3] Later, the newly blazed trail was widened and smoothed to the point where horse-drawn wagons or stagecoaches could use the road. The country's first successful long-distance stagecoach service was launched by Levi Pease along the upper road in October 1783.[4]

During the 19th century, turnpike companies took over and improved pieces of the road. Large sections of the various routes are still called the King's Highway and Boston Post Road. Much of the Post Road is now U.S. Route 1, U.S. Route 5, and U.S. Route 20.

Mileposts were measured from the intersection of Broadway and Wall Street in New York (one block west of Federal Hall) and from the old Boston city-line on Washington Street, near the present-day Massachusetts Turnpike.

The Metropolitan Railroad Company was chartered in 1853 to run streetcars down the stretch of the road on Washington Street in Roxbury, which is now served by the MBTA Silver Line. The Upper and Lower Boston Post Roads were designated U.S. Routes 1 and 20 in 1925 (though Route 20 has since been substantially modified).[4]

New York

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The Post Road in New York

Manhattan

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Much of the route in Manhattan, where it was known as the Eastern Post Road, was abandoned between 1839 and 1844, when the current street grid was laid out as part of the Commissioners' Plan that had been originally advanced in 1811.[5] The following sections of the road still exist:

These milestones were once present in Manhattan:

The Bronx

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The "Road to Kings Bridge, where the Rebels mean to make a Stand" in a British map of 1776

In southwestern Westchester County, now the Bronx, the Boston Post Road came off the Kings Bridge and quickly turned east, with the Albany Post Road continuing north to Albany, New York. It passed over the Bronx River on the Williams Bridge, and left The Bronx on Bussing Avenue, becoming Kingsbridge Road in Westchester County. In more detail, it used the following modern roads:

East and north towards West Farms Square
  • Kingsbridge Avenue – 230th Street – Broadway – 231st Street
  • Albany Crescent – Kingsbridge Terrace – Heath Avenue
  • gap across Jerome Park Reservoir
  • Van Cortlandt Avenue
  • gap at Williamsbridge Reservoir
  • Reservoir Place – Gun Hill RoadWhite Plains Road (southbound lanes)
  • gap from near 217th Street to near 231st Street
  • Bussing Avenue
  • gap from Grace Avenue to De Reimer Avenue
  • Bussing Place – Bussing Avenue

Westchester County

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The Boston Post Road entered what is now Westchester County on Kingsbridge Road, and turned north on Third Avenue-Columbus Avenue (Route 22), forking off onto Colonial Place. It continued across Sandford Boulevard (Sixth Street) where there is no longer a road, and curved east and southeast around the hill, hitting Sandford Boulevard-Colonial Avenue at the Hutchinson River Parkway interchange. It then continued east on Colonial Avenue-Kings Highway, merging with U.S. Route 1. From there to the Connecticut border, the Post Road used US 1, except for several places, where Post Road used the following roads:

  • The southbound side of US 1-Huguenot Street through downtown New Rochelle.
  • Old Boston Post Road north of downtown New Rochelle.
  • Old Post Road-Orienta Avenue south of downtown Mamaroneck.
  • Mamaroneck Avenue-Prospect Avenue-Tompkins Avenue north of downtown Mamaroneck.
  • Old Post Road at Playland Parkway in Rye.

Upper Post Road

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The Upper Post Road was the most traveled of the three routes, being the furthest from the shore and thus having the fewest and shortest river crossings. It was also considered to have the best taverns, which contributed to its popularity.[citation needed] The Upper Post Road roughly corresponds to the alignment of U.S. Route 5 from New Haven, Connecticut, to Hartford; Connecticut Route 159 from Hartford to Springfield, Massachusetts; U.S. Route 20 from Springfield to Warren, Massachusetts (via Route 67); Massachusetts Route 9 from Warren to Worcester; an unnumbered road (Lincoln Street in Worcester, Main Street in Shrewsbury, and West Main Street in Northborough) to Northborough; and U.S. Route 20 from Northborough to Boston. A series of historic milestones erected in the 18th century survive along its route from Springfield to Boston.

Connecticut

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Milestone 8 on the Upper Post Road in Harvard Square, Cambridge Massachusetts

Massachusetts

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Lower Post Road

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The Lower Post Road hugged the shoreline of Long Island Sound all the way to Rhode Island and then turned north through Providence to Boston. It traversed what is now the most densely populated part of Connecticut, including the state’s three largest cities; as a result, it is the best-known of the routes today. The Lower Post Road roughly corresponds to the original alignment of U.S. Route 1 in eastern Connecticut, Rhode Island, and Massachusetts.

Connecticut

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Rhode Island

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Massachusetts

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In Massachusetts, the Norfolk and Bristol Turnpike was established in 1803 as a straighter route between Pawtucket, Rhode Island, and Roxbury, Massachusetts, mostly west of the Post Road. It is known as Washington Street in many of the towns it passes through. [2] Due to its avoidance of built-up areas, the southern half of this road was little-used. In addition, another well-used route passed west of this turnpike along current Route 1A.

South Attleboro

The Post Road entered Massachusetts at the town of Attleboro's Newport Avenue (Route 1A) through the settlement of South Attleboro. It continued northeast on Newport Avenue along Route 123, splitting to the north (staying with Newport Avenue) to cross into North Attleborough.

North Attleborough

South of North Attleborough center, the old road is known as Old Post Road. The old road crossed the turnpike (now US 1) just south of the intersection with Route 120, forming a small curve before merging with the turnpike north of the intersection. This curved alignment is now gone, so traffic must use US 1. Additionally, US 1 leaves the turnpike at the Route 120 intersection to bypass North Attleborough center on East Washington Street.

The Lower Post Road passed through North Attleborough Center on Washington Street, later used as part of the turnpike. Another short curved alignment still exists to the west of Washington Street north of the center, now called "Park Street". Just north of this, the route crosses the Ten Mile River and then enters a complicated five-way intersection with US 1 and Route 1A. US 1 straight ahead is the old turnpike, and US 1 to the right was built in the 1930s. The Post Road went to the right onto Elmwood Street. The fork to the left onto Route 1A through Plainville center was an alternate route to Boston.

Elmwood Street enters the town of Plainville, where it becomes Messenger Street. The road merges with Route 106 before crossing Route 152 at Wilkins Four Corners and entering Foxborough.

Sharon

There is a road passing from the town of Sharon into East Walpole which is known as Old Post Road, which continues north as Pleasant Street into Norwood. [3]

East Walpole (part of Walpole)
Norwood

In Norwood, the oldest route of the Post Road followed Neponset Street south until the intersection with Pleasant Street. The newer route followed Washington Street through the center of Norwood, south towards Walpole.

Islington (part of Westwood)

The Post Road turned from East Street onto Washington Street, heading south towards Norwood.

Dedham

In Dedham, the road followed modern-day Lower East Street north to Boston. Here the Post Road splits, with the oldest route (prior to 1704) following East Street in an arc around the old marshes until it meets Washington Street (Route 1A) south of the Dedham village center.

The new road (in use by 1744) followed High Street to Court Street, and continued south along Highland Street and Elm Street, rejoining East Street south of Interstate 95.

Roxbury

In Roxbury, the road turned down Roxbury Street and followed modern-day Centre Street around the edge of Fort Hill, crossing Stony Brook at a bridge in the location of the modern-day Jackson Square MBTA station. The road continued following Centre Street southwards through modern-day Hyde Square and Jamaica Plain, and southwards to Dedham.

Boston

In the colonial city, the road began at the Old State House, the government center of the 18th-century city. Once called Cornhill, Orange, and Newbury Street, it's now modern-day Washington Street, running southwards off the Boston Neck towards the village of Roxbury.

Middle Post Road

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The Middle Post Road was the shortest, fastest, and youngest portion of the route. From Hartford, it ran into the Eastern Upper Highlands, an area with large native Indian populations. During King Philip's War of 1675, travel in these areas was often dangerous for settlers. It was not until the end of the war and establishment of the Colonial post system that the area began to become populated, and the middle post road was established as the fastest route. This area of the state continues to remain underpopulated in contrast to other portions of Connecticut, and accordingly, portions of the original post road have been preserved due to various circumstances. It split from the Upper Post Road in Hartford, and initially ran roughly along current U.S. Route 44 through Bolton Notch and towards Mansfield Four Corners. From Mansfield, it went through Ashford, Pomfret, and headed into Massachusetts via the town of Thompson, along Thompson Road. In Massachusetts, the Middle Post Road runs along sections of modern Route 16 to Mendon, then through Bellingham, and then via Route 109 from Medway to Dedham where it meets with the Lower Post Road (old U.S. Route 1) heading into Boston.

Connecticut

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Hartford

Starting at the Old State House, the road crossed the Connecticut River over the area that is now occupied by the Founders Bridge, initially by ferry and later by bridge. It is notable that until 1783, Hartford's eastern boundaries included present-day East Hartford and Manchester.

East Hartford

Although the road crossed via the route of the Founders Bridge from Hartford, this area was later developed into an enormous highway interchange, and thus much of the historic road was destroyed. In the early years of Connecticut's history, East Hartford was privately owned. What remains of the route is the path of Interstate 84 / Route 6, which connects to Manchester's Middle Turnpike East.

Manchester

Since Manchester was a part of Hartford until 1783, the area was made up of settlements and present-day boroughs. The post road can be traced along present-day Middle Turnpike East through central Manchester. It later passed through Manchester Green, where the post road became reconnected with Route 6, and, for the first time, U.S. Route 44. Just before leaving Manchester and entering Bolton, the post road breaks off Route 44 onto Middle Turnpike East (the portion of Route 44 between Manchester and Bolton is known as "New Bolton Road")

Bolton

Bolton serves a unique role in the post road, as it was the border between the flat and tranquil Connecticut River Valley, and the hilly and turbulent Eastern Upper Highlands. Entering Bolton on Middle Turnpike East, the traveler encountered a fork and could choose to head southeast on Bolton Center Street (later Center Street) to the settlement of Bolton, or stay on Middle Turnpike East to reconnect with Route 44 and head east on the original Mohegan Indian Trail through Bolton Notch, a natural depression in the ridge that dramatically sped up transit and served as a demarcation between the two geologic landscapes. Within the Bolton settlement was White's Tavern, notable for having housed the staff of General Rochambeau, whose unit camped in the settlement during the revolutionary war. To exit Bolton, one heads north on Notch Road until reaching Route 44, just outside Bolton Notch. Route 44 then connects to Coventry.

Coventry

Between Bolton and Mansfield, the road passed through the borough of North Coventry, entirely along present-day U.S. Route 44, known locally as the Boston Turnpike. Along the Willimantic River (and border of Mansfield) stands the Brigham Tavern, which holds the distinction of having housed George Washington around the period of the Revolutionary War. This plaque can be seen in front of the Brigham Tavern; it is currently a private residence.

Mansfield

Like Coventry, the post road follows the path of present-day U.S. Route 44. After crossing the Willimantic River from Coventry, the road crosses through Mansfield Four Corners, and towards Ashford.

Ashford

The road connects on Route 44 from Mansfield, and runs directly through the borough of Ashford. It stops, however, at Phoenixville, which then heads north towards Eastford on Route 198. Before reaching Eastford, however, it takes a right onto Route 244 ("Brayman Hollow Road") which headed directly to Pomfret.

Pomfret

At the center of Pomfret, Route 244 headed east turns into U.S. Route 44. The post road turns left shortly after the intersection with Route 169 onto Allen Road which quickly merges into Freedley Road. The road then heads northeast into Woodstock.

Woodstock

The post road briefly passes through the Harrisville section of town on Tripp Road before entering Putnam.

Putnam

Soon after entering Putnam, the road crosses over Route 171 onto West Thompson Road headed into Thompson.

Thompson

The post road soon follows over West Thompson Dam. The road once passed through the village of West Thompson, which was flooded purposely to control the Quinebaug River. The original post road can be seen from the Dam when water levels in West Thompson Lake are low enough. Once over the Dam the road turns into Route 193 and travels through historic Thompson Hill. Continuing northeast, the road bears right at a fork onto East Thompson Road and follows all the way to the Massachusetts state line.

Massachusetts

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Douglas

Crosses the Massachusetts state line into the town of Douglas as Southwest Main Street. This section passes through Douglas State Forest and is one of the most remote parts of the route that is still used as a public road. A 1-mile (1.6 km) section here was still unpaved until 2002. At the center of Douglas, the Post Road follows Massachusetts Route 16 eastward to East Douglas. Where Route 16 turns south, the Post Road continues east as Northeast Main Street, which leads to the Uxbridge town line. French General Lafayette traveled this road to join forces with Washington, and stopped in Douglas during the Revolutionary War.

The Stone Arch Bridge in Uxbridge, Massachusetts
Uxbridge

Entering Uxbridge, the name of the road changes to Hartford Avenue. Hartford Avenue is a major cross-town road and follows the route of the Post Road for its entire length. From the Douglas town line to the intersection of Massachusetts Route 122, it is known as Hartford Avenue West; from Route 122 to the Mendon town line, it is known as Hartford Avenue East. The original stone arch bridge over the Blackstone Canal is still in use today. There was a Civil War encampment near the stone-arch bridge, and the road was used by troops during the French and Indian Wars and as a supply route during the War of 1812. George Washington stopped here a number of times when traveling this road, including when he took command of the Continental Army at Boston in 1775, and on his post-Inaugural tour of New England in 1789.

Mendon

The Post Road enters the town from Uxbridge as Hartford Avenue West. It follows that road to Route 16, which follows the route of the Post Road for approximately one-half-mile eastward to Maple Street, which follows the route into Mendon town center. From there, the Post Road followed a Providence-Worcester post road south out of the village. This section is now part of Providence Street. About 1-mile (1.6 km) south of the town center the roads diverged. The Post Road heads east, now known as Hartford Avenue East. This road follows the original Post Road route to the Bellingham town line. Historic milestone 37 is still located along the route.[4]

Bellingham

The Post Road enters from Mendon as Hartford Avenue. Massachusetts Route 126 joins the road shortly before crossing over Interstate 495. Route 126 follows the Post Road route the remainder of the way to the Medway town line.

Medway

The original Post Road from Mendon followed Village Street through Medway to the Tavern and Inn in Medway Village near the Charles River. The post road followed (present day) Village Street through Millis (part of Medway until 1885). In the early 19th century, the Hartford and Dedham Turnpike was built (now Rt 109), a straight route built through the Great Black Swamp, and up a large hill in the center of town.

Millis

The original Post Road in Millis followed Village St from Medway, crossing current Massachusetts Rt 109, and then following the current Dover Road to the location of a series of Bridges over the Charles River leading into Medfield. In the period from 1806 to 1810, the Hartford and Dedham Turnpike was built (now Route 109), nearly going broke in attempting to build a causeway over the Charles River at the Medfield town line and through the Great Black Swamp.

Medfield
Dedham

The upper post road (US 20) also runs through Weston, and links directly to The Gifford School

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  • The Long Walk – a novel by Stephen King published under the pseudonym Richard Bachman in 1979 as a paperback original – revolves around the contestants of a gruelling walking contest along a route that roughly follows and extends beyond the Boston Post Road.
  • In the 1957 I Love Lucy episode "Lucy Raises Tulips", Lucy loses control of a riding lawn mower while mowing the lawn at the Ricardos' Westport home, and later describes riding it down the Boston Post Road "for a mile and a half, against traffic all the way".

See also

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References

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Further reading

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[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia
from Grokipedia
The Boston Post Road was America's first official postal route, established in 1673 to connect Boston, Massachusetts, with New York City, New York, over a distance of approximately 250 miles using preexisting Native American trails that facilitated early colonial communication and mail delivery by horseback riders, who typically completed the journey in about two weeks. This route, part of the broader King's Highway system active from the 1650s to 1735, evolved into three primary alignments: the Upper Post Road (the oldest, running inland through Hartford and Springfield and aligning with modern U.S. Routes 5 and 20), the Lower Post Road (a coastal path corresponding to U.S. Route 1), and the Middle Post Road (the shortest interior option, aligning with U.S. Routes 44 and 16). In the , the road gained further prominence as a conduit for news and commerce; it carried copies of the Boston News-Letter, America's first regularly published newspaper starting in 1704, and saw improvements under Deputy Postmaster General , who in 1753 surveyed the route to standardize mileage-based postal rates and oversaw the placement of enduring stone mile markers at one-mile intervals to aid travelers and postal workers. By 1783, the introduction of long-distance services transformed it into a vital artery for passenger travel, and in 1789, President traversed the full length during his inaugural tour of the new nation, underscoring its role in unifying the early . These developments highlighted the road's economic and informational significance, as post riders and later coaches ferried mail, passengers, and goods amid challenging terrain that included rivers, swamps, and forests. Over time, the Boston Post Road influenced the nation's transportation infrastructure; in the , segments were incorporated into the U.S. Highway System, including along the Lower path, and by the mid-20th century, portions formed the basis for interstate highways such as I-95 (Lower), I-91 (Upper), and I-84 (Middle). Today, remnants like the granite mile markers—many dating to Franklin's era and inscribed with distances to Boston—survive along the route in states including and , serving as tangible links to colonial and designated features in historic districts. The road's legacy endures as a foundational element of American connectivity, symbolizing the shift from rudimentary trails to modern roadways that continue to link the .

Historical Development

Colonial Origins

The Boston Post Road emerged from a network of preexisting Native American trails that early European settlers adapted for overland travel between the and emerging settlements to the south. By the mid-17th century, these paths had evolved into rudimentary roads connecting to points in and New York, facilitating trade, migration, and communication among Puritan communities. The route's development was spurred by the need for reliable intercolonial links following the English conquest of in 1664, which integrated Dutch trading paths into the colonial infrastructure. Organized postal service along what would become the Boston Post Road began in the Massachusetts Bay Colony in 1639, when the General Court appointed Richard Fairbanks' ordinary in Boston as the official place for depositing and exchanging letters, charging a fee for this service. This marked the first formal postal arrangement in British North America, predating broader intercolonial efforts. The true origins of the road as a designated post route trace to December 1672, when Francis Lovelace, governor of New York, proposed a monthly postal connection to Boston to John Winthrop Jr., emphasizing the route's importance for "intelligence" between colonies. The first post rider departed New York on January 22, 1673, traversing approximately 250 miles in two weeks on horseback, carrying mail and small packets along paths that hugged the coastline and inland valleys. The Massachusetts General Court supported this initiative in 1673 by ordering compensation for messengers at three pence per mile and designating relay points. By the late 17th century, the Boston Post Road had formalized into multiple parallel paths through , reflecting terrain and settlement patterns: the Upper Post Road via and Springfield for inland travel, the Lower Post Road along the shoreline through New Haven and Fairfield for coastal access, and an emerging Middle Post Road in the 1690s connecting directly to via Tolland and Woodstock. These routes were incorporated into the broader King's Highway system, a 1,300-mile colonial network laid out between 1650 and 1735 to link major ports from to Charleston. Postal service was interrupted by in 1675–1676 and resumed in the 1690s. In 1691, a royal patent from William and Mary granted Thomas Neale a monopoly on the colonial for 21 years, with Andrew Hamilton appointed as deputy in 1692 to oversee operations, including improvements to the New York-Boston line. Postal riders continued monthly service, often on foot or horseback, with the road's milestones and bridges gradually added to ease passage through swamps and rivers. The road's colonial significance lay in its role as America's inaugural dedicated mail route, enabling the rapid dissemination of news, such as the 1704 Boston News-Letter, the colonies' first newspaper, which relied on post riders for distribution. It also supported commerce by allowing merchants to send bills of exchange and goods samples. Travelers like Sarah Kemble Knight documented the route's challenges in her 1704 journal, noting muddy paths, hostile terrain, and sparse inns, underscoring its evolution from trail to essential colonial lifeline. By the early , under figures like as from 1753, the road featured standardized rates and stone mile markers, solidifying its for the Revolutionary era.

18th and 19th Century Developments

In the early , the Post Road solidified into three primary routes—Upper, Lower, and Middle—facilitating more reliable postal and travel services between and New York, evolving from rudimentary paths into designated highways used by post-riders on horseback. By 1753, , as , oversaw the placement of stone mile markers along the route to standardize distances and improve for carriers and travelers. During the Revolutionary War, the road played a crucial role in , including the 1775 transport of cannons from to under , which helped force the British evacuation. Post-war, in 1783, the road was widened and smoothed to accommodate America's first long-distance service, reducing travel time from over a week to about two days and marking a shift from horse relays to wheeled transport. The introduction of stagecoaches in the late 18th century spurred further enhancements, with operators like Levi Pease launching services that carried passengers, mail, and goods, fostering commerce along the route through and . In 1789, President traveled the full length during his New England tour, stopping at taverns and highlighting the road's growing national importance as a connector of emerging urban centers. By the early 19th century, turnpike companies began acquiring and upgrading sections, paving stretches with and building bridges, such as the 1798 Harlem River bridge in New York, which shortened the route by over four miles and reduced tolls for efficiency. Stagecoach traffic peaked around 1830, with up to 40 coaches weekly traversing the road, equipped with Concord designs for greater speed and comfort, averaging 8-10 miles per hour and supporting economic ties in trade hubs like and New Haven. As railroads emerged in the , such as the New York and New Haven line completed in 1849, stagecoach usage on the Boston Post Road declined sharply, though the route retained local significance for short-haul travel and continued to influence regional development until the late . Turnpike investments had by then transformed the road into a network of improved highways, with milestones and toll gates ensuring maintenance and funding for ongoing repairs against seasonal wear. In 1827, there were 26 stage routes operating within and through . This era cemented the Boston Post Road's legacy as a foundational for American communication and mobility, bridging colonial paths to modern .

The Road in New York

Manhattan

The Boston Post Road in served as the southern terminus and initial segment of the colonial mail route connecting to , established in 1673 as America's first intercolonial postal system under New York Francis Lovelace. Originally tracing Native American paths and designated a public in 1669, it functioned as the island's primary thoroughfare during the , known variously as the Eastern Post Road or King's Highway, facilitating mail delivery, trade, and travel before the imposition of the Commissioners' Plan street grid in 1811. This route was critical for colonial communication, with post riders covering the distance in stages, often changing horses at inns along the way. The road's path through Manhattan began at the southern tip near the Battery and proceeded northward along what are now Park Row and the , then veered eastward along the Boston Road—today's —through midtown. In , particularly around , it realigned onto between roughly 110th and 145th Streets before returning to Broadway near 169th Street, crossing the via McComb's Dam (present-day 155th Street) or Kings Bridge at the island's northern end to enter . These segments evolved from irregular trails into more defined paths by the mid-18th century, supporting services that began in 1783 and accelerating regional connectivity. To standardize distances, , as colonial , ordered the placement of 12 granite in 1769 along the route from , with several positioned in to guide travelers on the primitive roads. Surviving examples include the Eleventh in Roger Morris Park (originally at 170th Street in 1769 and relocated to 189th Street by 1819), inscribed to denote miles from New York on the Kingsbridge Road, and the Twelfth at Isham Park's entrance in Inwood, marking the final mile on the island. During the , the road held strategic importance as a conduit for news of events like the protests in 1765 and the in 1773, while also serving as a military ; British forces captured it in 1776, and American troops reclaimed it on Evacuation Day in 1783. By the , obscured much of the original path, though remnants like these preserve its legacy as a foundational of early American .

The Bronx

The Boston Post Road enters The Bronx from Manhattan at Kingsbridge, near the modern intersection of Broadway and West 228th Street, following an ancient Native American trail that facilitated early colonial travel and mail delivery. Established as part of America's first official postal route in 1673 under Colonel Francis Lovelace, the road traversed rural landscapes through what was then Westchester County, including the area now known as The Bronx, before crossing the Bronx River at Williamsbridge and continuing northeast toward Westchester. This segment, roughly aligning with portions of today's U.S. Route 1, played a crucial role in connecting New York City to Boston, with post riders taking up to two weeks to cover the full distance by horse. Following the , the route through was significantly rerouted in the late by , a signer of the Declaration of Independence and owner of vast estates in Morrisania, to pass through his lands and improve connectivity. The revised path shifted eastward, incorporating segments now known as Boston Road, which runs from the through areas like Claremont Village and Allerton, bounded by modern streets such as Home Street and Jackson Avenue near Youth Village Playground. This adjustment, formalized around 1792, transformed the road into a more direct thoroughfare, supporting travel and local commerce while crossing key landmarks like the Bronx River via the historic Eastchester Bridge. During the Revolutionary War, the road saw military use, including by couriers like , who traversed its unpaved, rugged stretches multiple times as a messenger for the Continental Congress. In its modern form, the Boston Post Road in is fragmented but traceable along Boston Road, interrupted by developments like the Bronx Zoo and Pelham Parkway, before rejoining north of Bronx-Pelham Parkway. , as colonial in 1753, ordered the placement of stone milestones along the route to standardize distances, some of which may have marked Bronx segments though few survive today. The road's legacy endures in local nomenclature, such as in Soundview—a park commemorating the historic path—and in its evolution from a bone-jarring trail to a vital artery for 19th-century horse railways and early suburban growth, until railroads diminished its prominence by the 1840s. Connections like Gun Hill Road provided shortcuts linking it to the Albany Post Road, aiding travel between Yonkers and eastern Bronx areas during colonial times.

Westchester County

In Westchester County, the Boston Post Road enters from via Road, following what is now largely northward along the county's coastal plain toward . The route traverses a series of towns including Eastchester, , Pelham, New Rochelle, Mamaroneck, Larchmont, Rye, and Port Chester, paralleling and incorporating segments of older paths like the Westchester Path, an indigenous trail used by Native American groups for millennia before European settlement. Established as part of the colonial postal system in 1673, this section served as a critical for delivery, trade, and travel between and , with post riders covering the distance in stages that included overnight stops at local taverns. The road's origins trace to pre-colonial indigenous routes, such as the Westchester Path documented in early 20th-century archaeological surveys in New Rochelle and Rye, which revealed camp sites and stone implements along its alignment. By the late 17th century, it was formalized under English colonial governance, with the first organized mail service beginning in 1673 under Governor Francis Lovelace, who dispatched riders biweekly from New York to Boston via Westchester's settlements. Improvements accelerated in the 18th century; milestones were erected along the route in 1763 at the direction of Benjamin Franklin, then deputy postmaster general, to aid navigation and measure distances. During the American Revolution, the road became a strategic corridor: British forces under Howe landed nearby in 1776, leading to the Battle of Pell's Point on October 18, 1776, near Pelham, where colonial troops under Colonel John Glover delayed the advance and protected Washington's retreat. The area around Rye, designated a "Neutral Ground" by Washington in 1778, saw ongoing skirmishes between Patriots and Loyalists, underscoring the road's role in the conflict. Key taverns along the Westchester stretch provided essential respite for travelers, including military figures. Guion's Tavern in Eastchester hosted , who was reportedly nursed by landlady Mrs. Guion during an illness, while Johnson's Tavern near West Farms and Haviland's in served as hubs for stagecoaches and post riders into the early . Infrastructure enhancements continued post-Revolution; the Westchester Turnpike, chartered in 1800, straightened and widened portions through New Rochelle and Mamaroneck, facilitating faster coach travel, and Coles Bridge over the Hutchinson River (built 1798) improved connectivity. By the , the road spurred suburban growth in villages like Mamaroneck, where commercial development clustered along its length, including nurseries and inns that catered to increasing traffic. Today, much of the historic alignment is preserved within the Boston Post Road Historic District in , a 286-acre designated in 1993 for its architectural and Revolutionary War associations. This district encompasses five properties, including the Jay Estate (built 1838 in Greek Revival style on land owned by since 1745), Whitby Castle (a Gothic Revival mansion completed 1856 by architect ), and the Marshlands Conservancy, highlighting the road's evolution from a rugged to a landscaped corridor amid 19th-century estates. Archaeological evidence within the district reveals continuous use from prehistoric eras through the colonial period, with artifacts dating to 3000–4999 BCE. While modern carries heavy traffic, parallel parkways like the (opened 1930s) bypassed congested sections, allowing preservation efforts to focus on interpretive markers and restored sites that commemorate the road's foundational role in American connectivity.

Upper Post Road

Connecticut

The Upper Post Road in Connecticut represented the inland segment of the original colonial mail route from New York to , spanning roughly 35 miles northward from New Haven to along the valley. Established in 1673 under the direction of New York Francis Lovelace, it became the most traveled of the three post roads due to its relatively straight path and avoidance of coastal hazards, serving as America's first intercolonial . The first post rider covered the full 250-mile journey from New York to , including this Connecticut portion, in about two weeks, carrying letters and small packages on horseback. This route followed pre-existing Native American trails, evolving into a vital corridor for , migration, and communication by the late . It loosely aligns today with , passing through early settled communities that supported travelers with ferries across the and other rivers, as well as taverns and blacksmiths. In the , the mandated towns along the road to erect stone distance markers—at least two feet high—to aid navigation and indicate miles to county seats, though fewer survive compared to the coastal lower road. The road played a crucial role in colonial and Revolutionary War logistics, transporting news of British troop movements and supplies between New Haven's port and Hartford's political centers. Notable figures, including during his 1753 postal survey, traversed it to standardize rates and routes under the 1691 . By the early , turnpikes improved sections for stagecoaches, but railroads soon supplanted it; remnants persist in historic districts and markers, underscoring its foundational impact on Connecticut's connectivity.

Massachusetts

The Upper Post Road in Massachusetts formed the eastern segment of the most heavily traveled branch of the Post Road, connecting Springfield in the west to in the east, a distance of approximately 90 miles. Established as part of America's first organized postal system in 1673 under the direction of New York Governor Francis Lovelace, this route followed ancient Native American trails, including the Pequot Path, and evolved into a vital for mail delivery, trade, and military movement. It entered from near Stafford Springs, passing through towns such as Sturbridge, Southbridge, Charlton, , Auburn, and Worcester before continuing eastward via , Westborough, Northborough, Marlborough, Framingham, Natick, Wellesley, Newton, and Brookline to reach . By the early , the Upper had become a primary thoroughfare for post riders on horseback, who covered the full New York-to-Boston distance in relays of about 60 miles per day, delivering mail biweekly. In 1734–1735, surveyor Alexander Ireland erected the first stone milestones along the portion at the behest of the provincial , marking distances from to aid travelers and postal efficiency; notable surviving examples include the Milestone 8 in Cambridge's (originally placed nearby in 1734) and others in Weston and Marlborough. These markers, inscribed with distances and Ireland's initials "A.I.," facilitated standardized postal rates and operations, which by the 1780s offered regular service with inns spaced every 10–15 miles, such as the Golden Ball Tavern in Weston (built 1760s). During the , the route played a critical role in logistics, most famously as part of Henry Knox's in the winter of 1775–1776, when forces hauled 59 cannons from through Springfield and along the Upper Post Road to besiege British-held , contributing to the city's evacuation in March 1776. The road's infrastructure improvements, including bridges over the Chicopee and Quaboag Rivers near Springfield and Palmer, supported this effort and later economic growth, fostering settlements and commerce in . By the early , turnpikes like the Worcester Turnpike (incorporated 1801) paralleled and upgraded sections from Worcester to , reducing travel time from days to hours via horse-drawn coaches. In the , the Upper Post Road largely aligns with , designated in 1926 as part of the federal highway system, which bypasses some original alignments but preserves the corridor's path through and Worcester Counties. Preservation efforts include the 1983 listing of the Boston Post Road Historic District in Weston on the , encompassing 18th-century homes, taverns, and mile markers that illustrate and rural life. This segment underscores the road's enduring role in connecting Boston's urban core to the Valley, influencing regional development from to industry.

Lower Post Road

Connecticut

The Lower Post Road in formed the coastal segment of the original colonial mail route from New York to , spanning approximately 110 miles eastward from the New York border to the line along the shore of . Established in 1673 under the direction of New York Francis Lovelace, it followed preexisting Native American trails through densely settled coastal communities, serving as a vital corridor for mail delivery, trade via ports like New Haven and New London, and travel, though challenged by tides, swamps, and river ferries. The first post rider covered the full 250-mile journey from New York to Boston, including this Connecticut portion, in about two weeks, carrying letters and small packages on horseback. This route passed through early towns such as Stamford, Norwalk, Fairfield, Bridgeport, Stratford, Milford, New Haven, Branford, Guilford, Old Saybrook, Old Lyme, New London, Groton, and Stonington, with ferries aiding crossings over inlets and rivers like the at Old Saybrook. By the late 17th century, it had evolved into a key pathway for commerce and communication, supported by taverns, inns, and blacksmiths in shoreline settlements. In the , the required towns to maintain the road and erect guideposts, though stone mile markers were less common here than on inland routes. The road was essential for colonial and Revolutionary War activities, facilitating the transport of news, supplies, and troops along the coast, including to New London's shipbuilding center. surveyed it in 1753 as deputy to standardize rates and routes under the 1691 . By the early , turnpikes enhanced sections for stagecoaches, but railroads eventually overtook it; remnants survive in historic districts, markers, and preserved alignments underscoring its role in Connecticut's coastal connectivity.

Rhode Island

The Lower Post Road entered Rhode Island from , crossing into Westerly and following the coastal path northward along what is now largely U.S. Route 1. From Westerly, the route proceeded through Charlestown and South Kingstown—passing landmarks such as —before reaching North Kingstown, including the village of . It then continued via East Greenwich and to Providence, where it turned inland toward . This shoreline-hugging alignment, formalized as part of the colonial postal system in the late , measured approximately 30 miles within the state and relied on ferries for short crossings, such as to Jamestown near Newport, though the primary path avoided a direct traverse of . Established in 1673 as one of America's earliest mail routes, the segment of the Lower built upon preexisting Native American paths, including elements of the Pequot Trail, to connect coastal settlements for postal riders and travelers. By 1707, it was designated a formal under British colonial authority, with post riders carrying mail and newspapers like the Boston News-Letter between New York and . In 1753, , as deputy postmaster general, surveyed the route through during a tour to standardize distances and improve efficiency, leading to the placement of granite mile markers—some of which survive today along sections like in North Kingstown. The road supported services starting in 1783, reducing travel time from to New York to about four days and fostering economic ties through taverns and inns, such as those in and . The route's significance extended to military and cultural exchanges during the Revolutionary War, serving as a supply line for patriot forces and a path for figures like George Washington, who traveled it in 1775 en route to Cambridge. In Providence, it intersected with key wharves, amplifying the city's role as a trade hub. Today, remnants include historic structures like the Hall-Northrup House in North Kingstown and the Old Narragansett Church site off Shermantown Road, preserved amid 20th-century straightening for automobiles. Efforts by local historical societies continue to highlight its legacy, though commercial development along Route 1 poses preservation challenges.

Massachusetts

The Lower Post Road in formed the northeastern segment of the coastal branch of the , connecting the border near Attleboro to , a distance of approximately 45 miles. Established as part of America's first organized postal system in 1673 under the direction of New York Governor Francis Lovelace, this route followed ancient Native American trails along the southern edge of the state and evolved into a vital for delivery, , and passenger travel through more populated suburban areas. It entered from at Attleboro, passing through towns such as North Attleborough, Plainville, Wrentham, Foxborough, Sharon, Stoughton, Canton, Dedham, and Brookline before reaching . By the early , the Lower Post Road served post riders on horseback, who covered the full New York-to-Boston distance in relays of about 60 miles per day, delivering mail biweekly along this shorter, more direct path compared to inland alternatives. While fewer stone milestones were placed here than on the Upper route, some and distance markers aided navigation, supporting standardized postal rates and the growth of operations by the 1780s, with inns like those in Dedham spaced for travelers. During the , the route played a key role in , serving as a supply line for Continental forces and traversed by during his 1775 journey to and 1789 inaugural tour. Its proximity to coastal ports and urban centers facilitated news dissemination and economic activity in southeastern Massachusetts. By the early , turnpikes such as the Dedham and Turnpike upgraded sections, shortening coach travel times; railroads later supplanted it for long-distance transport. In the , the Lower Post Road largely aligns with , incorporated into the federal highway system in 1926, preserving its corridor through and Counties despite bypasses. Preservation efforts highlight historic sites along this path, including 18th-century structures in Dedham and Brookline, illustrating colonial settlement patterns and the road's influence on from to suburban growth.

Middle Post Road

Connecticut

The Middle Post Road in Connecticut formed the northeastern segment of the shortest branch of the Boston Post Road, veering eastward from through the Windham Hills to the Massachusetts border, spanning approximately 50 miles. Established in the 1690s as new towns were settled in northeastern , it connected Hartford to Boston via an interior path that avoided the coastal hazards of the Lower Post Road and the longer detour of the Upper Post Road through Springfield. This route followed preexisting Native American trails and became a key corridor for mail delivery, trade, and migration, though it was less traveled than the Upper due to its challenging terrain described as "very rocky, bushy, in many places miry" by traveler Benjamin Wadsworth in 1694. The path passed through towns such as , , Tolland, and Woodstock, supporting early colonial communication with post riders carrying letters and packages on horseback, completing the full New York-to-Boston journey in about two weeks. In the , the required towns along post roads to erect stone distance markers for navigation, though fewer survive on this interior alignment compared to the coastal route. surveyed the Middle Post Road in 1753 as Deputy , standardizing mileage for postal rates and overseeing the placement of mile markers to improve efficiency. During the colonial era and , the road facilitated the transport of news, supplies, and personnel between Hartford's political centers and eastern settlements, contributing to regional connectivity amid swamps, hills, and forests. By the early , turnpikes upgraded sections for stagecoaches, but railroads later overshadowed it; today, remnants align loosely with , passing through historic communities with preserved markers and districts that highlight its role in Connecticut's early infrastructure.

Massachusetts

The Middle Post Road in Massachusetts comprised the eastern terminus of the shortest alignment of the , entering from near Woodstock and extending approximately 70 miles to through southern Worcester and Counties. Developed in the late as part of the evolving postal network under the 1673 system initiated by New York Governor Francis Lovelace, this interior route utilized ancient Native American paths and served as a direct alternative to the longer Upper Post Road via Springfield. It passed through towns including Thompson (at the border), , , Sutton, Mendon, Milford, Bellingham, Franklin, , Medfield, and Dedham before reaching , fostering trade and settlement in less coastal areas. By the early , post riders traversed the Middle Post Road in relays, delivering mail biweekly along with early newspapers like . The route's challenging landscape of hills and wetlands limited its use compared to the Upper, but improvements under in 1753 included stone mile markers at one-mile intervals to standardize rates and aid navigation; some inscribed markers from this era survive in towns like Mendon. Inns and ferries supported travelers and stagecoaches, which by the provided regular service, with establishments spaced every 10-15 miles. In the , the Middle Post Road supported logistics for Continental forces, carrying dispatches and supplies between and strongholds, though less prominently than the Upper route. Infrastructure enhancements, including bridges over rivers like the Quinebaug near Thompson, aided military and economic movements, promoting growth in . Early 19th-century turnpikes, such as those paralleling sections from Mendon to , accelerated coach travel; later, railroads diminished its prominence. Today, the Middle Post Road loosely corresponds to U.S. Route 16 from to Mendon, then local roads and U.S. Route 109 through to Dedham, integrated into the 1926 U.S. Highway System and influencing interstates like I-495. Preservation includes historic districts and markers, such as those in Mendon, emphasizing its contribution to regional development from colonial trails to modern connectivity in the .

Legacy

Preservation and Historic Sites

The Boston Post Road, as one of America's earliest postal routes, has benefited from extensive preservation initiatives aimed at protecting its physical remnants, associated structures, and historical markers. Efforts include designation of historic districts under the and status, coordinated by state historic preservation offices and the . These designations emphasize the road's role in colonial communication, Revolutionary War logistics, and 19th-century development, while addressing threats from modern development and urban expansion. Local commissions in , , and New York enforce guidelines to maintain architectural integrity and scenic qualities along surviving segments. In , the Upper Post Road features the Boston Post Road Historic District in Weston, listed on the National Register in 1983, encompassing 760 acres and over 170 buildings from the 18th to 20th centuries, including the Golden Ball Tavern (1768) and the First Parish Church. This district preserves the best intact section of the state's colonial east-west connector, with well-maintained Georgian, Federal, and Greek Revival structures that reflect rural settlement patterns. Preservation involves strict zoning to prevent incompatible development, ensuring the road's alignment remains visible amid parks, cemeteries, and taverns. A prominent feature statewide is the series of 34 granite mile markers, erected beginning in 1767 to guide travelers, with 26 in along routes through Worcester and ; these were refurbished by the in collaboration with preservation firms like Daedalus Inc., involving cleaning, repositioning (e.g., the 54-mile marker in ), and protection from vehicular damage to highlight their Revolutionary-era significance. Connecticut's segments, part of both the Upper and Lower Post Roads, include the Boston Post Road in Darien, added to the National Register in 1980, which protects 26 structures around the First Congregational Church (1837) and (1910), illustrating architectural evolution from pre-Revolutionary farmsteads to commuter-era homes. In Madison, the Commission safeguards properties along the road as tangible links to colonial trade and settlement. The Old Post Road in Fairfield, established in 1962 and overlapping National Register boundaries, preserves 17th-century homes and taverns, with ongoing surveys by the Connecticut Trust for to document and nominate additional sites. Along the Lower Post Road in Rhode Island, preservation focuses on individual structures like the former Kentish Artillery Armory at 3259 in , built in 1912 and now housing the Warwick Center for the Arts, which originated in 1974 as part of bicentennial efforts and maintains its historic character through . The Historical Preservation & Heritage Commission lists related properties in and North Kingstown, emphasizing the road's brief but vital coastal link. In New York, the Boston Post Road Historic District in Rye, designated a National Historic Landmark in 1993, spans 286 acres with three pre-Civil War mansions—"The Locusts" (c. 1745, Jay family estate), "Alansten" (1838), and "Whitby" (1854)—plus the Jay Cemetery and Marshlands Conservancy, highlighting 19th-century elite architecture and indigenous history dating back 10,000 years. Managed by the Jay Heritage Center and New York State Parks, preservation includes land donations (e.g., 120 acres in 1967) and restoration to combat deterioration, integrating the site into Westchester County's African American Heritage Trail for broader interpretive programs.

Cultural and Modern Significance

The Boston Post Road holds enduring cultural significance as a symbol of early American connectivity and identity formation. Established in the late as the nation's first postal route, it facilitated the rapid dissemination of revolutionary ideas between and New York, contributing to the cohesion of the colonies during the lead-up to the . Historians note that its role in linking distant communities helped inhabitants "start making people realize they were ," fostering a shared national consciousness beyond local loyalties. This legacy is highlighted in the 2018 PBS documentary 10 Streets That Changed America, which portrays the road as a pivotal "information superhighway" that spurred political and social transformations, from colonial correspondence to the birth of the first successful American newspaper, the Boston News-Letter, in 1704. In , the Boston Post Road appears as a setting in Stephen King's 1979 dystopian novel The Long Walk (published under the pseudonym ), where it serves as the grueling route for a fictional endurance contest in a totalitarian America, traversing modern from southward. The road's historical path underscores themes of perseverance and societal control, drawing on its real-world reputation as a demanding colonial . Beyond literature, it features in historical narratives like Eric Jaffe's 2009 book The King's Best Highway: The Lost History of the Boston Post Road, from Its Founding to the , which explores its evolution as a cultural artery shaping four centuries of American life, from stagecoaches to suburban sprawl. Today, the Boston Post Road's modern significance lies in its integration into , a vital corridor for , , and daily commuting between major Northeast cities, handling millions of vehicles annually while paralleling Interstate 95. Though overshadowed by interstates for long-distance efficiency, segments retain their historic name and attract tourists seeking Revolutionary-era sites, including preserved 18th-century mile markers—stone posts erected to guide travelers—and colonial taverns repurposed as inns. The actively preserves these markers, such as those visible near the Spencer Country Inn, supporting that draws history enthusiasts to explore the road's tangible links to the nation's founding. Efforts to maintain these artifacts emphasize the route's ongoing role in educating the public about early infrastructure's impact on and mobility.

References

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