Midway, KY: Horses, History, and Small-Town Charm

Tucked into the rolling hills of Kentucky’s Bluegrass region, Equus Run Vineyard and Winery is a peaceful escape perfect for wine lovers and weekend wanderers. Set on 38 acres of scenic countryside, this winery invites visitors to explore the grounds with a self-guided map, enjoy a picnic, or simply kick back on the deck with a glass in hand.

Highlights:

• 38-acre vineyard in Kentucky’s scenic Bluegrass region
• Self-guided tours with maps available at the gift shop
• Winery tours and guided tastings of locally made wines
• Outdoor deck and picnic garden
• Bonus: a small putting green for a bit of fun

Pro Tip:

Bring your own picnic and grab a bottle from the tasting room—the outdoor deck and garden area make for a great afternoon hang.

Equus Run Vineyard and Winery, 1280 Moores Mill Rd, Midway, KY 40347
Phone: 859-846-9463
equusrunvineyards.com

Want to really soak in the spirit of Kentucky’s horse country? Unbridled Horse Tours is your ticket. Run by local expert Martha Martin, a lifelong Kentuckian with deep roots in the thoroughbred world, these custom tours take you behind the scenes of the Bluegrass Region. Whether you're into breeding farms, bourbon distilleries, or historic landmarks, Martha will tailor your day to match your interests—and you’ll leave with a deeper love for Kentucky.

Highlights:

• Customized private tours of Kentucky horse country
• Led by Martha Martin, a true local with lifelong industry experience
• Visits can include stud farms, bourbon stops, and historic sites
• Flexible, personalized itineraries
• Great for first-time visitors or seasoned horse lovers

Pro Tip:

Let Martha know your favorite things—horses, history, or bourbon—and she’ll craft an unforgettable day packed with local flavor and insider stories.

Unbridled Horse Tours, Midway, KY 40347
Phone: 859-333-8940
unbridledhorsetours.com

If you're curious about where Kentucky's legendary horse racing roots began, Airdrie Stud is the place to go. Nestled along scenic Old Frankfort Pike, this historic Thoroughbred breeding farm has deep ties to the very foundation of the industry—home to the legendary Lexington and five Kentucky Derby winners. Today, it’s still producing elite racehorses and welcomes visitors for private, behind-the-scenes tours.

Highlights:

• Birthplace of some of Kentucky’s greatest racehorses
• Private 2-hour tours of the farm and breeding facilities
• Meet promising young thoroughbreds and famous bloodlines
• See state-of-the-art stalls and historic grounds
• Friendly, knowledgeable staff with stories to share

Pro Tip:

Tours fill up fast, so book ahead—and don’t forget your camera. The horses (and the rolling hills) make for some seriously beautiful photo ops.

Airdrie Stud, 2641 Old Frankfort Pike, Midway, KY 40347
Phone: 859-873-7270
airdriestud.com

Where to Eat

You really can’t leave Midway without treating yourself to a meal at the Holly Hill Inn. A true local landmark since the 1800s, this charming spot has served as everything from a farmhouse to a tavern—and now, it’s a beloved fine dining destination. Guests come for the ever-changing 4-course degustation menu and the popular Sunday Brunch, both built around the freshest local, seasonal ingredients.

Highlights:

• Historic inn with roots dating back to the mid-1800s
• Seasonal 4-course tasting menu
• Beloved Sunday Brunch with rotating local favorites
• Dedicated to showcasing fresh, regional ingredients
• Home of the Holly Hill Wine Guild with pairing events

Pro Tip:

If you're a wine lover, check out one of their Wine Guild events—you'll get to enjoy perfectly paired bites in a relaxed, elegant setting.

Holly Hill Inn, 426 N. Winter Street, Midway, KY 40347
Phone: 859-846-4732
hollyhillinn.com

A favorite with locals and visitors alike, The Brown Barrel and Blind Harry’s serve up hearty American classics with a side of small-town charm. Named after two legendary Midway figures, this laid-back spot is all about good food, strong drinks, and great company. The menu has something for everyone—from topped Tater Tots and beer-battered mushrooms to fresh salads, stacked burgers, and satisfying entrées.

Highlights:

• Casual American dining in a welcoming atmosphere
• Appetizers like Nachos and Tater Tots with a twist
• Salads, sandwiches, burgers, and hearty entrees
• Small Plates and sides for lighter cravings
• Full bar with creative cocktails and Kentucky bourbon

Pro Tip:

Pair your meal with a pour of local bourbon or try one of their house cocktails—great way to kick back and soak up that Midway hospitality.

The Brown Barrel and Blind Harry’s, 224 N. Gratz Street, Midway, KY 40347
Phone: 859-403-2003
thebrownbarrel.com