Leiper's Fork is located along the Natchez Trace, which was an important travel route for Native Americans and early European-American settlers.

The area was settled in the late 1700s by settlers from North Carolina and Virginia who had received land grants as payment for service in the American Revolution.

It is believed that the Hillsboro name was already in use for a community in Coffee County, so the post office was given the name of Leiper's Fork for the stream that runs through the village.

[2] Commercial businesses in Leiper's Fork include inns and restaurants, antique stores, a woodworking shop, private art galleries, and real estate offices.

These include music festivals, annual turkey shoots in November,[8] and model airplane competitions in September.

[11] The annual "Almost Famous Leiper's Fork Christmas Parade," the second Saturday in December, is known as a "quirky" array of animals, classic cars and country fun.