Things to Do in Winchester, KY

By VI | Disclosure: I use affiliate links

The City of Winchester

Craving a quiet getaway with small-town charm, bourbon heritage, and scenic drives? I say head to Winchester, Kentucky—you’ll be glad you did. Just a short drive east of Lexington, Winchester has given me some of the warmest Southern welcomes I’ve ever experienced. It’s where rolling bluegrass hills meet local flavor, and you can slow down without missing a thing. From beer cheese tastings to stops on the bourbon trail, I’ve found Winchester to be one of those places that stays with you long after you leave.

Best Time to Visit

If you’re planning your trip, I highly recommend coming between April and October. I’ve visited during spring and fall, and both offer gorgeous Kentucky scenery—blossoms in spring and golden hills in autumn. Summer brings local festivals, farm visits, and long, sunny days perfect for exploring. No matter when you go, you’ll find something worth savoring.

How to Get There

By Car: I usually drive in via I-64—it’s just 25 minutes from Lexington and about 1.5 hours from Louisville. The route is scenic and simple.
By Plane: When I fly, I use Blue Grass Airport (LEX) in Lexington. It’s a quick 30-minute drive to Winchester, and I always suggest renting a car to make the most of your trip.
By Bus: Regional buses can get you to Lexington, but I’ve always found a car or rideshare to be the easiest way to reach Winchester directly.

Where to Stay

Hampton Inn Winchester – I’ve stayed here for its comfort and convenience. The indoor pool and free breakfast are great perks, especially if you’re on the go like I usually am.
Red Roof Inn Lexington – Winchester – If you’re traveling on a budget, this spot is simple, clean, and just minutes from everything. I’ve used it as a base for bourbon tours and scenic drives.
Local Airbnbs – I’ve spent a few nights in cozy country homes and lofts near Main Street, and you should too. They offer charm and character you just can’t get from a chain hotel.