Boone There, Done That!
Winchester’s Labor Day weekend comes with dancing, a downtown 5K and more than 130 booths packed onto Main Street, which is a fairly convincing reason to leave the house before summer slips away.
Main Street Takes Over
The 47th annual Daniel Boone Pioneer Festival fills downtown Winchester on Saturday, Sept. 5, and Sunday, Sept. 6, with arts, crafts, food and the kind of sidewalk wandering that can turn a quick visit into an afternoon.
Shopping hours run from 10 a.m. to 5 p.m. both days, with more than 130 booths lining Main Street. A free children’s area gives families somewhere to redirect extra energy, while food vendors handle the equally important matter of keeping everyone fed.
The weekend actually starts a little early. On Friday, Sept. 4, a street dance runs from 7 to 10 p.m., giving Winchester a head start on the festival before the booths open Saturday morning.
Saturday begins on a more athletic note with the GRC Cross Country Daniel Boone 5K Honoring David Borden. The race starts at 8:30 a.m. at the corner of Lincoln and East Hickman streets, then follows an out-and-back course that turns around near the country club.
Anyone planning to run or walk can register for the Daniel Boone 5K for $30. Registration remains open until race time, though runners who want a shirt need to sign up by Aug. 22.
Leave the Parking Puzzle to the Shuttle
Downtown festivals are fun. Downtown festival parking can become its own competitive event.
Organizers have made that part easier with free shuttle service from two locations: RDC at 620 Boone Ave. and Conkwright Elementary School at 360 Mt. Sterling Road. Shuttles run from 9:30 a.m. to 6 p.m. Saturday and Sunday, giving visitors a way to skip some of the circling and get straight to Main Street.
Once there, the weekend is built for lingering. Browse the booths, grab something to eat, let the kids burn off some energy and return the next day if you missed half of what you meant to see.
After 47 years, the Daniel Boone Pioneer Festival clearly knows how Winchester likes to spend Labor Day weekend: outside, downtown and with plenty going on.
For more Kentucky festivals worth building a weekend around, explore the Guide to Kentucky directory at https://www.guidetokentucky.com/festivals.
