This fall, let Winchester be your home base for all the exciting adventures Central Kentucky has to offer! Whether you’re heading out for a day at Keeneland Race Course, exploring the natural beauty of Red River Gorge, enjoying vibrant fall festivals, or cheering on the Kentucky Wildcats, Winchester is perfectly positioned to offer you the best of both worlds—action-packed days and relaxing nights.
Just a short drive from all the region’s top attractions, Winchester invites you to experience small-town charm with big-time hospitality. After a day of adventure, unwind with a cozy dinner at one of our local restaurants, sip on craft drinks, and stroll through our historic downtown. Relax in comfortable accommodations that let you recharge for the next day’s exploration.
If you end up sticking around in Winchester, explore all of the local shopping options, fun lunch spots, and plenty of things to do outdoors!
We’re Perfectly Positioned for Amazing Fall Fun for the Entire Family!
Keeneland Race Course: Witness the thrill of horse racing at its finest, then retreat to Winchester for a quiet evening away from the crowds.
Red River Gorge: Spend the day hiking, climbing, and taking in the breathtaking fall scenery, and return to Winchester for a restful night.
Fall Festivals: From pumpkin patches to harvest celebrations, explore the region’s festivals, then savor Winchester’s small-town charm and local flavors.
UK Football: After cheering on the Wildcats, escape the hustle and bustle with a short drive to Winchester, where a cozy dinner and laid-back vibe await.
With its ideal location, welcoming atmosphere, and vibrant dining and lodging options, Winchester is the perfect place to relax after your day of fall fun.
Plan Your Fall Trip Today!
Don’t wait—book your stay in Winchester and experience the best of Central Kentucky this season. Whether you’re here for a weekend or an extended stay, Winchester offers the perfect balance of adventure and relaxation.
Your fall getaway starts here!