Do & See

Dip into an ooey-gooey cheesy Winchester original—tangy-delicious beer cheese. Sip a ginger- and citrus-flavored soda. Browse one-of-a-kind shops and boutiques in the nostalgic, yesteryear ambience of a “Main Street USA” downtown. Savor local flavors from diner-style cooking to comfort food goodness to upscale delicious.

Take in a show at our premier performing arts center or visit a museum for a beautiful presentation of regional history. Enjoy a game of disc golf or traditional golf on a championship course. Connect with nature while camping, kayaking or visiting an ADA-accessible historic preserve park. From arts enthusiasts to nature lovers, Winchester entices and entertains.

Visit wineries, a brewery, distillery and roastery. Dig into Civil War history on driving and walking tours. Roll along the river, into the country and through downtown on cycling tours.

Check-in and stay awhile at a Winchester cabin, cottage, campground or hotel for adventures to nearby natural wonder, Red River Gorge, and Daniel Boone’s former stomping grounds at Fort Boonesborough State Park.