Eat & Drink

Pull up to a “Big Boy Breakfast Special” near Pilot Knob, where Daniel Boone got his first eyeful of Kentucky’s Bluegrass Region, a Smoked Gouda Hot Brown at a place where Helen Keller once spoke, an artisanal pizza in the building once occupied by the Rough and Ready Firefighters of the 19th century or a Beer Cheese Burger at the site where the story of beer cheese began nearly 100 years ago.

Winchester has an abundance of local restaurants dishing up an array of culinary experience, with a helping of history on the side.

From cupcakes, donuts and local brews—of both the coffee and craft beer varieties—to oven-baked deli sandwiches and “world-famous” pork belly sandwiches, deep-fried catfish to salt rock-seared pork steak, Winchester delicacies tempt hungry diners, no matter what their foodie fave-crave may be. Thirsty? As home to the only soft drink invented in Kentucky, Winchester has been quenching thirst with the inimitable Ale-8-One (the official soft drink of Kentucky) since 1926.

And Winchester does it in style—with a hearty mix of neighborhood watering holes, easily-missed-but-well-worth-the-trip holes-in-the-wall, historic buildings, favorite local haunts (some of which are haunted), downhome diners, upscale eateries and one exclusive trail. As in the one and only Always Original Winchester Beer Cheese Trail®, where more than a dozen secret-recipe beer cheese dishes may be enjoyed.

Whether traveling from near or far, come on in. Let Winchester serve you up something special.