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A day trip to Woodford County

From dive bars to glittering restaurants, and everything in between, we’ve got the ultimate itinerary for a day trip to Woodford County.

Molly and Aayat standing in the dining room at The Glitz with twinkly lights and ornaments

Happy to fill the role of ladies who lunch. | Photo by LEXtoday

Table of Contents

In honor of Hallmark movie season, we couldn’t pass up the opportunity to shine a light on our own sweet small town neighbors in Woodford County. After all, Midway is a legitimate Hallmark movie town thanks to 2019’s “Midway to Love.”

Whether you want a quick day trip or a mini getaway, here’s everything you need to know about the area + our insider recommendations.

A shot of downtown Midway from the street corner with colorful awnings.

Find local shops, restaurants, and museums in downtown Midway. | Photo by @jimbobarnett


Things to do
Bluegrass Distillers at Elkwood Farm, 158 W. Leestown Rd. | See the newly restored 1830s mansion + farm property, which will also debut its “grain to glass” experience in early 2024.

Thoroughbred Theatre & Wine Bar, 127 E. Main St. | Sip local wine while taking in live performances including comedy shows, music, and plays, or brave the stage yourself on open mic nights.

Grub to eat
Gibson’s, 131 E. Main St. | The fully loaded menu with pastas, steaks, and salads has something for everyone, plus the downstairs tavern is open late with karaoke on Saturdays.

Heirloom, 125 E. Main St. | Try dine-in or take-out French-inspired dishes like mussels, meatballs, and duck fat fries.

Holly Hill Inn, 426 N. Winter St. | Upscale dining with a cozy southern twist, you’ll feel right at home in the historic house-turned-restaurant thanks to the culinary creative minds of the Holly Hill & Co. team.

Midway Bakery, 510 S. Winter St. | Satisfy your sweet tooth with a variety of freshly baked pies, cookies, brownies, and breads.

Local sips

Black Type Co., 137 E. Main St. | Sip and stay a while with coffee, wine, and cocktails all in one spot.

Equus Run and Saddlestone Distillery, 1280 Moores Mill Rd. | There’s no shortage of spirited fun at these sister properties, where you can savor sips of wine and agave-based pours, and brandy.

A historical marker for Watkins Tavern in front of downtown Versailles

We love the reuse of historical buildings in Versailles’ downtown. | Photo by LEXtoday


Things to do

Woodford Reserve, 7785 McCracken Pike | Tour the beautiful grounds, learn about the distilling process, and toast to the good life at one of the leading bourbon brands in the Bluegrass.

Rail Explorers, 175 Beasley Rd. | Pedal your way along the Louisville Southern Railroad to see unique views of the Kentucky River gorge, area horse farms, and distilleries.

Bites of the Bluegrass, Locations vary | Explore the flavors of Woodford County with Chef Ouita Michel on the Just a Few Miles South Culinary Tour.

Ouita Michel Cooking School, 167 S. Main St. | A cooking lesson with the queen of Kentucky kitchens...need we say more? Be sure to stop by on Saturdays to shop during its retail hours.

The Kentucky Castle, 230 Pisgah Pike | From holiday tours, to goat yoga, to spa treatments + farm-to-table meals, you can spend all day in this royal setting.

Grub to eat

Wallace Station, 3854 Old Frankfort Pike | Nestled along a scenic byway, you can fuel up on southern sandwiches like hot ham + cheese, chicken salad, and catfish.

Wilson’s Pool Haul, 131 Lexington St. | If you’re looking for a more laid-back vibe, stop by for pool, darts, cheap burgers and beer.

J&B Food Mart, 200 Lexington St. | Don’t let its gas station location deter you, word from a local is that this place has the best fried chicken.

The Glitz, 4205 Fords Mill Rd. | A true treat for all the senses, you’ll enjoy a three-course meal among the glittering bright lights and decor. The family-owned restaurant is hidden below the unique antiques of the Irish Acres Gallery.

Vallozzi’s, 108 Court St. | Using ingredients flown in from Italy each week, sample fresh fare such as calamari, burrata, seafood, salads, and pastas.

Local sips

The Amsden, 151 S. Main St. | This dreamy cafe has coffee for the grown-ups, hot cocoa for the littles, with storytime + shopping for the whole family.

The Amsden Bourbon Bar, 106 Court St. | Here’s where you can find the perfect nightcap with 100+ bourbons, specialty cocktails, wine, and beer.

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