Guidebook for Winchester
Parks & Nature
Fort Boonesborough State Park
4375 Boonesboro RdRed River Gorge
John Holder Trail
1225 Athens Boonesboro RdLegacy Grove Park
1107 W Lexington AveJust a 30 min drive to enjoy this Kentucky favorite.
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Kentucky Horse Park
4089 Iron Works PkwyJust a 30 min drive to enjoy this Kentucky favorite.
Three Trees Canoe-Kayak
300 Athens Boonesboro RdFood scene
Hall’s is widely known as a Kentucky tradition.
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Hall's On The River
1225 Athens Boonesboro RdHall’s is widely known as a Kentucky tradition.
We love this place. Look them up on Facebook for live music events.
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Waterfront Restaurant and Lounge
220 Athens Boonesboro RdWe love this place. Look them up on Facebook for live music events.
Smokin' Howards Sports Bar & Grill
20 North Main Street
Loma's
103 South Main StreetEngine House Pizza Pub
9 W Lexington Ave
La Trattoria
30 North Main StreetBlue Isle Home-Style Restaurant and Bar
410 Boone AvePictures don’t do this place justice. We love the macaroons, breakfast Sammy, big cookies, and so many fun flavors of cupcakes.
Cupcake Apothecary
808 Bypass RoadPictures don’t do this place justice. We love the macaroons, breakfast Sammy, big cookies, and so many fun flavors of cupcakes.
Wildcat Willy's Distillery and Restaurant
31 E Broadway StShopping
Sugar Belle's Boutique
21 S Main St
Betsey's Boutique Shop
18 North Main StreetYou won’t leave empty handed.
A must see in our charming downtown. Original art, handcrafted bow ties, antiques, vintage accessories, so much to see.
Mason on Main
70 South Main StreetA must see in our charming downtown. Original art, handcrafted bow ties, antiques, vintage accessories, so much to see.
Brewery/Distillery
Live music is scheduled frequently in the summer.
Wildcat Willy's Distillery and Restaurant
31 E Broadway StNew location near the farmers market on Depot Street.
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Abettor Brewing Company
128 N Highland StNew location near the farmers market on Depot Street.
Winery
Harkness Edwards Vineyards
5199 Combs Ferry RdTalon Winery & Vineyards
7086 Tates Creek RdGrimes Mill Winery
6707 Grimes Mill RdJean Farris Winery & Bistro
6825 Old Richmond Rd
Hamon Haven Winery
7041 Rockwell RoadSightseeing
Bluegrass Heritage Museum
217 S Main StFall Meet 2022 October 7-29
Breeders Cup Nov 4-5
Spring Meet April 7-28 2023
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Keeneland Race Track station
Fall Meet 2022 October 7-29
Breeders Cup Nov 4-5
Spring Meet April 7-28 2023