- Our list of the best things to do in Winchester, Kentucky, features the top 73 nearby activities — including 36 great attractions with user approval ratings of 90% or more!
- Winchester, KY has a variety of great sights and experiences nearby. Top categories include: Outdoor Places, Museums & Galleries, Sights & Landmarks, and Entertainment & Shows.
- The results below include the top 11 things to do within the city of Winchester, KY , followed by 63 popular activities in nearby cities, including Lexington, Richmond, Nicholasville, Georgetown and Paris
Showing 21-30 of
201
15.6 Miles
Built in 1891, the Cane Ridge Meeting House is one of the oldest churches in the state and also its largest one-room construction.
16.0 Miles
Visitors can taste wine at a historic 18th century farmhouse and enjoy tours across a 5 acre vineyard at Talon Winery & Vineyards. The tasting room features a unique barrel ceiling.
16.6 Miles
91%
280 votes
120 Sycamore Road, Lexington, KY 40502
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Ashland: The Henry Clay Estate is a large historical mansion that has been wonderfully preserved. Guests can travel back to the 18th century when Henry Clay and his family lived in the 18-room mansion through self-guided tours or those led by a docent.
16.8 Miles
Horse Farm Tours is a service that provides its guests with a unique experience touring premier Thoroughbred horse farms. In addition to viewing the horse farms, visitors also visit the Historic Keeneland Race Course as well as other local attractions.
17.3 Miles
At Thoroughbred Park, visitors can pose with life-sized bronze plaques of horses and their riders. The park features over 40 sculptures of famous historical figures in racing with informational plaques.
17.6 Miles
With a long history in Lexington, the Kentucky Theater currently shows plays, new movie releases, classic movies, concerts, and more. The interior, which was recently restored, is opulently decorated with golden stained glass, chandeliers, and gold lion moldings.
17.6 Miles
As a historic theater, Kentucky Theatre is filled with classic architecture and showcases a mix of independent and blockbuster hits. The concession stand serves popcorn, and alcoholic beverages like wine and beer.
17.7 Miles
As a culinary tour, Bleu Plate Tours takes visitors on a walking excursion to the major cultural eateries that the city has to offer. Each tour has at least six stops and provides samples of each cuisine.
17.7 Miles
Founded in 1780, Transylvania University is a private university known for its extensive Greek life offerings, with over 70% of its students enrolled in a fraternity or sorority. The institution, whose name athletic rival is Centre College, features a library that was dedicated by Dwight D. Eisenhower.
17.7 Miles
The University of Kentucky is a public research university that offers a variety of academic programs for its students to complete at the Bachelor's, Master's, and doctorate levels. The location is also the home of the Kentucky Wildcats, an SEC athletic program known for winning several NCAA basketball champion…