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Fun Things To Do In Winchester, KY

Attractions, Sightseeing and Events


Find fun things to do in Winchester, KY. View our list of attractions, activities, events, restaurants and visitor information. 

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Blackfish Bison Ranch
Blackfish Bison Ranch
Tour in Winchester, KY USA

Blackfish Bison Ranch provides guided tours of buffalo herd. Blackfish Bison Ranch provides guided tours of our buffalo herd. We transport you by pickup or wagon to our buffalo where you can feed them by hand. Tours last approximately 1 hour. Bus tours are welcome and have easy access. Reservations are required.


Bluegrass Heritage Museum
Bluegrass Heritage Museum things to do on a rainy day in Lexington, KY
Museum in Winchester, KY USA

history museum Rolling grassland, wood and stone fences, tobacco, horses and unparalleled beauty make Kentucky's Bluegrass Region one of the most beautiful places to visit in all of the United States.

Bluegrass Heritage Museum
Bluegrass Heritage Museum things to do on a rainy day in Lexington, KY
Museum in Winchester, KY USA

Museum with rich heritage of Central Kentucky The Bluegrass Heritage Museum brings the history of the area to life for both the old and young by collecting, preserving and exhibiting objects valuable to the history of Winchester, Clark County and the Bluegrass region of Kentucky.

Civil War Fort at Boonesboro
Civil War Fort at Boonesboro
Historic Site in Winchester, KY USA

earthwork fortification was built by Union Soldiers The earthwork fortification was built by Union Soldiers to defend the ford and ferry at Boonesboro. A scenic trail provides a beautiful view of the Kentucky River.

Guided Cell Phone Tours
Guided Cell Phone Tours
Recreation in Winchester, KY USA

cell phone guided tour Modern technology provides you with a knowledgeable companion as you explore Winchester’s past.


Hamon Haven Winery
Hamon Haven Winery things to do on a rainy day in Lexington, KY
Winery in Winchester, KY USA

winery Nestled in the heart of the Bluegrass is a charming, family owned winery that produces eight hand-crafted, award-wining wines.

Holly Rood- Clark Manson
Holly Rood- Clark Manson things to do on a rainy day in Lexington, KY
Historic Site in Winchester, KY USA

Historic Home Built in 1814 by James Clark, 13th Governor of Kentucky, the house follows the simple lines of Federal style architecture. Tours by appointment.

Leeds Center for the Arts
Leeds Center for the Arts things to do on a rainy day in Lexington, KY
Historic Site in Winchester, KY USA

historic theater The Leeds Theatre is a single-screen movie theater in downtown Winchester, Kentucky. One of Winchester's first movie houses, the theater was purchased by S.D.

39th Annual Daniel Boone Pioneer Festival
39th Annual Daniel Boone Pioneer Festival
Labor Day Weekend, Sep 01, 2017 (Friday) to Sep 03, 2017 (Sunday) Festival event in Winchester, KY USA

Labor Day weekend celebration! The festival begins with a street dance on Friday evening and continues throughout the weekend with: Arts and Crafts, Talent Contest, 5K Run, and a Walk with Friends. The finale is the Sunday evening concert featuring nationally known country music entertainers.


9th Annual Beer Cheese Festival
9th Annual Beer Cheese Festival
Jun 10, 2017 (Saturday) Festival event in Winchester, KY USA

Beer Cheese Tasting Festival Ask almost anyone what the best part of the Beer Cheese Festival is, and they'll tell you, "Sampling beer cheese!" and they're right. We start at 10am and go all the way to 5pm. You can sample beer cheese from any of our vendors. Sample them all. Find your favorite.

Civil War Living History Event
Civil War Living History Event
Jun 24, 2017 (Saturday) History event in Winchester, KY USA

-12th United States Colored Heavy Artillery -Reactivated with Cannon Fire on the hour -Numerous re-enactors and demonstrators -Be sure to bring your walking shoes...

Halloween MAINia
Halloween MAINia
Halloween, Oct 31, 2017 (Tuesday) Children event in Winchester, KY USA

Downtown Winchester Trick or Treat Halloween MAINia is traffic free Trick or Treat event in our historic Downtown Winchester! Join us from 6:00pm until 8:00pm for Halloween fun! All are welcome to this Free and Family Friendly event.

Rock the Block Concert Series
Rock the Block Concert Series
May 26, 2017 (Friday) to Aug 25, 2017 (Friday) Concert event in Winchester, KY USA

2nd Annual Summer Concert Series on Main Street

Sip-N-Stroll
Sip-N-Stroll things to do on a rainy day in Lexington, KY
Sep 14, 2017 (Thursday) Food event in Winchester, KY USA

Annual wine tasting event "Sip & Stroll"! Join us for our annual wine tasting event "Sip & Stroll" featuring Kentucky Wineries hosted by our incredible downtown merchants.

Winchester -Clark County Tourism Commission
Winchester -Clark County Tourism Commission
Tourism in Winchester, KY USA

Visitor's Center

Baymont Inn & Suites Winchester
Baymont Inn & Suites Winchester
Hotel in Winchester, KY USA
Currently as low as $59.99/night!

The hot breakfast indoor pool and free Wi-Fi draw guests to the Quality Inn and Suites Winchester located off I-64 22 miles outside of Lexington. All 47 rooms at the two-story Quality Inn feature free Wi-Fi cable TV microwaves and refrigerators. Free Internet, Swimming Pool, Indoor Pool, Free Breakfast, Non Smoking Rooms.

Best Western Winchester Hotel
Best Western Winchester Hotel
Hotel in Winchester, KY USA
Currently as low as $70.83/night!

Offering a complimentary hot breakfast free Wi-Fi and cable TV the Best Western Winchester Hotel provides Priceline guests a practical choice 17 miles from Lexington. Swimming Pool,Outdoor Pool, Free Breakfast, Pets Allowed, Non Smoking Rooms.

Christmas Parade
Christmas Parade
Dec 02, 2017 (Saturday) Children event in Winchester, KY USA

Downtown Winchester KY Christmas Parade

Comfort Inn Winchester
Comfort Inn Winchester
Hotel in Winchester, KY USA
Currently as low as $59.20/night!

Boasting a complimentary hot breakfast indoor pool free Wi-Fi and cable TV the non-smoking Comfort Inn Winchester earns high praise. The 58 non-smoking rooms at the three-story Comfort Inn feature free Wi-Fi and cable TV. Free Internet, Indoor Pool, Non Smoking Rooms.

Hampton Inn Winchester
Hampton Inn Winchester
Hotel in Winchester, KY USA
Currently as low as $139.00/night!

The hot breakfast Wi-Fi connection and cable TV are on the house at the Hampton Inn Winchester located 22 miles outside of Lexington. The 59 rooms of the two-story Hampton Inn feature convenient lap desks free Wi-Fi and cable TV. Non-smoking rooms are available. Free Internet, Swimming Pool,Outdoor Pool, Non Smoking Rooms.

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