Winchester was founded in 1793. Our main street (still a vital part of the community), is lined with beautiful Victorian styled architecture. Daniel Boone remains the favorite son and just minutes from downtown you’ll find Fort Boonesborough. It’s the areas’ oldest settlement. Enjoy the Daniel Boone Pioneer Festival held each Labor Day weekend featuring both locally and nationally known entertainers, a street dance, arts and crafts, food vendors, fireworks and much more. If bluegrass music sets your toes to tapping, then join us for the Bluegrass Heritage Festival & Burgoo Cook-Off held the second weekend in October.
Family farms continue to line the countryside while manufacturing has become our primary livelihood. Winchester is proud of our heritage and working hard to build on the foundations laid by our founding fathers.