Stranraer (Scottish Gaelic: An t-Sròn Reamhar [ən̪ˠˌt̪ʰɾɔːn ˈɾãũ.əɾ]), also known as The Toon or The Cleyhole, is a town in Dumfries and Galloway, Scotland, on Loch Ryan and the northern side of the isthmus joining the Rhins of Galloway to the mainland. Stranraer is Dumfries and Galloway's second-largest town, with a population of 10,593.

Stranraer is the administrative centre for the Wigtownshire area of Dumfries and Galloway. It was formerly a ferry port, connecting Scotland with Belfast and Larne in Northern Ireland; the service was transferred to nearby Cairnryan in 2011. It lies 87 miles (140 km) south-west of Glasgow, 52 miles (84 km) south-west of Ayr and 72 miles (116 km) west of Dumfries.

The name comes from Scottish Gaelic, An t-Sròn Reamhar, meaning "the broad headland" or "the fat nose".

The Battle of Loch Ryan was fought near Stranraer on 9/10 February 1307 during the Scottish Wars of Independence. King Robert I of Scotland's invasion of his ancestral lands in Annandale and Carrick began in 1307. The Annandale and Galloway invasion force was led by his brothers Alexander de Brus and Thomas de Brus, Malcolm McQuillan, Lord of Kintyre, an Irish sub-king and Sir Reginald de Crawford. The force consisted of 1,000 men and 18 galleys. They sailed into Loch Ryan and landed near Stranraer.

The invasion force was quickly overwhelmed by local forces, led by Dungal MacDouall, who was a supporter of the Balliols, Comyns and King Edward I of England, and only two galleys escaped. All the leaders were captured. MacDouall summarily executed the Irish sub-king and Malcolm McQuillan, Lord of Kintyre. Alexander, Thomas and Reginald de Crawford were sent to Carlisle, England, where they were executed. The heads of McQuillan and two Irish chiefs were sent to King Edward I.

On 12 November 1595, the Clashant of Stranrawer was named part of Ninian Adair's lands of Barony and, in 1596, was erected into a burgh of barony, the Barony of Kinhilt. This is recorded in the Register of the Great Seal of Scotland. The partial translation into English is:

At Linlithgow, 12 November 1595, the King confirms and for faithful service again dedicates to Ninian Adair of Kinhilt, and the legitimate male heirs of his body, which failing his nearest legitimate male heirs whosoever bear the name and insignia of Adair[, various lands....] In addition, the King creates the village at Clauchane de Stranraer as a free burgh of the barony with a free port, called the Burgh and Port of Stranraer; and the said Ninian etc shall have the authority to appoint a bailiff, treasurer, Dean of Guild, magistrate, burgesses, officials etc; and the burgesses shall have the authority and leave to pack and unpack [meaning the selling of bulk merchandise (wholesale trade) allowed by law only by free men in a free burgh], to buy and sell [also allowed only in a free burgh] etc; [...] and the said Ninian etc shall have authority to hold the position of governor of the said burgh, [...] to hold weekly markets on Saturday, with free (untaxed) market days twice a year, viz Saint Barnabas' day the 11th of June, and at Peter's Imprisonment called Lammas on the 1st of August, [...] and the said Ninian etc shall have authority over all the port customs of the said burgh raised by sea or land among the land tenents of the said burgh and support of the said port; and the said Ninian etc shall have authority to receive resignations of lands of the said burgh etc [i.e. recover his lands from towns people who choose to sell them or give them up]; from those persons whatsoever who chose to dispose of them; the townspeople may meet three times a week on Monday, Wednesday and Friday.

By 1600, Stranraer had become the market town for western Wigtownshire. Around this time, Stranraer was reached by a military road built from Dumfries to allow easier access to Portpatrick for transportation of people to Ireland for the Plantation of Ulster. Stranraer became a royal burgh in 1617.