Enterprise is a city in the southeastern part of Coffee County and the southwestern part of Dale County in Southeastern Alabama, United States. Its population was 28,711 at the 2020 census. Enterprise is the primary city of the Enterprise micropolitan statistical area (with the portion of the city in Dale County part of the Ozark micropolitan statistical area). It was originally a part of Enterprise–Ozark micropolitan area before being split; for a longer while it was originally part of the Dothan-Enterprise-Ozark combined statistical area but is now its own separate primary statistical area in later censuses.

Enterprise is famous for the Boll Weevil Monument, a large monument of a woman holding a boll weevil, in the middle of Main Street. The city erected the statue because the destruction of the cotton crop by the boll weevil had led to agricultural diversity, starting with peanuts and more prosperity than had ever come from cotton alone. It is the only statue to an insect pest in the world. Enterprise is right outside the U.S. Army's Fort Rucker, the home of Army Aviation.

Enterprise is home to Enterprise State Community College.

The founder of Enterprise, John Henry Carmichael, first settled there in 1881. Carmichael opened a store, which attracted more settlers to the area, and by the next year, a post office was relocated from the settlement of Drake Eye to the north to Enterprise. In 1896, with 250 people having settled there, the city of Enterprise incorporated. Soon afterward, the Alabama Midland Railway came to Enterprise, bringing with it opportunities for commerce and growth. By 1906, its population had grown to 3,750.

Enterprise's way of life came under threat in 1915. An infestation of boll weevils found its way into the region's cotton crops, resulting in the destruction of most of the cotton in Coffee County. Facing economic ruin, the nearly bankrupt area farmers were forced to diversify, planting peanuts and other crops in an effort to lessen the damage and recoup some of their losses.

Two years later, Coffee County was the United States' leading producer of peanuts. Not only did Enterprise stave off disaster, but its economy was renewed by the thriving new crop base. In appreciation, the people of Enterprise erected a monument in the city center to what the monument calls their "herald of prosperity", the boll weevil. The Boll Weevil Monument was dedicated on December 11, 1919, as a reminder of how the city adjusted in the face of adversity. It is the only monument to an agricultural pest in the world.

In the early afternoon of March 1, 2007, Enterprise was struck by a violent EF4 tornado. The tornado caused nine deaths and injured over 121 others. Damage in Enterprise was estimated at nearly $307 million, the worst disaster in the city's history.

The most severe damage occurred at Enterprise High School, where eight students died after a hallway was destroyed and the wall collapsed on them. The students were Michael Bowen (16), Andrew (AJ) Jackson (16), Ryan Mohler (16), Peter Dunn lll (16), Michael (Mikey) Tompkins (17), Jamie Vidensek (17), Michelle Wilson (16) and Kathryn Strunk (16). Enterprise resident Edna Strickland was killed in her home near the high school, the ninth fatality from the tornado. A quarter mile-wide swath through the downtown area was devastated, with at least 370 houses damaged or destroyed. The National Guard was called into the city; a dusk-to-dawn curfew was implemented immediately after the disaster. President Bush arrived the morning of March 3 and immediately declared Coffee County a disaster area. An AmeriCorps team was sent to the city to help organize and participate in disaster relief.