How to Have The Ultimate Girls’ Weekend in Shelbyville, Kentucky

Shelbyville isn't just for backelor parties.
Shelbyville isn't just for backelor parties. Courtesy Shelbyville Tourism

Kentucky isn’t just for bachelor parties. The smaller towns of 2019 are increasingly cozy, culture-filled gems bursting with culinary and beverage explorers, quirky shops and storefronts, and a whole lot of local charm. Case in point: Shelbyville.

Shelbyville is a secret women’s powerhouse of the Bluegrass State. Kentucky’s only current female master distiller works at Jeptha Creed. Mainstreet is full of women-owned shops, and the town is home to a famous first math and sciences school for women of the Commonwealth.

We continue to find things to love about Shelbyville, and as the town grows, the options only get better. From historic buildings and refurbished lofts to lauded chefs and distillers, Shelbyville has a lot to do. We collected our favorite things to see and do to give you an action-packed itinerary for one of Kentucky’s best weekend getaways.

Where to Stay

Shelbyville’s downtown is home to some of the most beautiful AirBnBs in Kentucky. The second-floor spaces have been painstakingly decorated and in some cases restored, with gorgeous exposed brick work and large, sunny windows.

The best AirBnB right now has to be Saddlebred Suites, a sprawling, modular space that can sleep as many as 17 if the entire space is rented (single or double rooms are available as well most of the year). A coffee shop is scheduled to open downstairs later this year, so it’s easy walking in the morning to get moving (that is, if you can stand to leave).

What to Do:

Drink bourbon, of course! While the newly opened Bulleit Distillery experience in Shelbyville will no doubt draw large crowds with its new sensory tasting program, one of the most interesting distilleries in town is the significantly smaller, family-owned and mother-daughter operated Jeptha Creed.

Jeptha recently released the first batches of their 2-year-old bourbon, and with the release has come a significant upgrade to their VIP cocktail making classes. Most of Jeptha Creed’s best tours, including barrel tastings and cocktail classes, are offered exclusively through Mint Julep Tours, but even the distillery tour and tasting is loaded with extras.

The Nethery family has, in just a few years, put out an impressive stable of liqueurs, brandies, and of course whiskeys, and almost all of them are regularly available for tasting. So even if your group has a whiskey-averse member, they’ll be able to find something to enjoy. And be sure to check the schedule for events; Jeptha Creed regularly hosts bands and live acts under their free Jammin’ at Jeptha! Series.

In addition to the distilleries, Shelbyville is at the heart of some of the best horse breeding territory in the country, with plenty of farms to visit (try and go during foal season if you can, because, well, adorably baby horses).

There are a few nightlife options in town, including bars and a great taco place, but our pick for a chill, easy-going nightcap is The Barrel Room. They’re a beer-focused spot with about a dozen custom and local brews on tap, including a few barrel-aged selections. The bar also has a surprising bourbon selection lovingly curated by the owners. Barrel Room has live acts on the weekends, and while they don’t serve food, they’ve got a stack of menus and allow ordering in—a smart option for large groups that one comfort food before bed.

Where to Eat

The Old Stone Inn is a landmark in and of itself. Built in 1792, the space has been many things, but most recently it has risen up the ranks as one of the hidden gem restaurants in the region.

If there’s one reason to go to Old Stone Inn (and there are many more than that), it’s for the dessert menu. Owner David Danielson, who you may know as the Executive Chef at Churchill Downs, has lovingly recreated an heirloom recipe: Appalachian Apple Stack Cake: a warm, country-style apple layer cake served with rosemary brown butter ice cream.

You’ll want to save room for this despite the main offerings ($22-$31), which include beef short ribs, a variety of fish and shrimp and grits.

Danielson’s whisky list is quite impressive, and his prices are fair, but if you’re going for a drink, be sure to inquire about their unique ice program, which we won’t spoil the story of here.

Science Hill Inn is a tasteful, upscale restaurant located at the site of the historical Science Hill Female Academy, a math and science school for girls founded in 1825. The school’s old buildings now double as a series of antiques shops and a few onsite restaurants, including the Inn. It’s a great lunch spot, quiet at times but with excellent southern staples.

Historic Bell House is also good for quick light bites, with a lean toward fresh produce and home-cooking staples.

Where to Shop

On Main Street, Polkadotted Pineapple is worth setting aside a few minutes for. It’s a diverse collection of women’s fashion including a fair amount of Derby-apporpriate hats and dresses, and a few things for the guys, if you’re looking for gifts. Make sure to also check out the The Shops at Gatsby, which are a group of indoor storefronts with a variety of things to browse. And check out EightTwenty8, especially if you’re looking for bridesmaid gifts, souvenirs, or an extra, last-minute wardrobe change option.

A note for anyone with a sweet tooth: you must, must make a stop into Serendipity Kandy Kitchen. In addition to some recognizable pre-packaged brands in the front of the store, this place has an array of homemade sweet treats that might cause some buyer’s anxiety. We found it had to choose between chocolate-dipped potato chips, white chocolate dipped Little Debbie Oatmeal Cream Pies, and a homemade chocolate covered, bourbon-filled Twinkie garnished with pecans.

We went for the Twinkies, which were light and fluffy with pronounced bourbon flavor (they were also gone very quickly).

There’s plenty more shopping to do off Main Street, however, in the form of a designer outlet mall. The Outlet Shoppes of the Bluegrass houses outlet shops from names like Gucci, Tory Burch, Brooks Brothers, Coach, The North Face, and Saks Fifth Avenue, plus tons of food options.


Where to Recharge

Regardless of which morning you find time, make sure to stop through Brick+Mortar Boutique and Coffeehouse just a few minutes down the road from main street for great coffee, breakfast, or perhaps a delicious cinnamon bun (check their calendar as hours change seasonally). The space is cute, quiet, and unpretentious, great for planning the day (or recovering from the night).

Their iced coffee is excellent, and if you really need something for your hangover, you’ll have the opportunity to order the Elvis: a peanut butter and banana sandwich that we regretted not ordering the second we saw one with our own eyes.

G. Clay Whittaker
Clay is Editor at Large of The Bourbon Review. He has written about whiskey, food, drink, and culture for Esquire, Playboy, Men's Journal, Popular Science, Southern Living, Maxim, among others.