After you’ve done your tastings and toured your favorite distilleries, you might be asking yourself, “Now what?” While bourbon is obviously the crown jewel of the Bourbon Trail, the towns those distilleries call home are packed with Kentucky-fried experiences worth adding to your itinerary.

In towns like Shelbyville, Georgetown (the Birthplace of Bourbon!), and Simpsonville, you’ll find locally owned shops lining downtown streets, restaurants housed in historic mansions, and local watering holes packed with friendly locals.

So after you’ve gotten your Bourbon Trail passport stamped, here’s how to experience the rest of what makes Kentucky great.

Where to Stay

Accommodation options along the trail range from Hiltons and Marriotts (for anyone looking to cash-out those points) to renovated 1870s farmhouses, charming B&Bs, and boutique hotels.

Bottled in Bond is a spectacular rental property above Main Street in downtown Shelbyville. A late-1800s clothing factory transformed into a swanky loft, the digs feature custom furniture, exposed brick, a suspended fireplace, and a dining table crafted from Jim Beam distillery wood to keep the bourbon-soaked theme flowing. It’s also walkable to everything downtown, which certainly matters when you’ve been bouncing between tastings all day. 

If you’re interested in more wide-open spaces, Harbison House is a renovated 1870s farmhouse that belonged to the current owner’s grandparents. Situated less than 10 minutes from Shelbyville, it comes complete with claw-foot tubs and a chef’s kitchen. 

Bardstown’s The Trail Hotel is the newest option—a resurrected property with swanky interiors and modern amenities that include a pool, a golf simulator, and even a Bourbon Butler ready to help consult on all things Bourbon Trail. 

Where to Eat

Upscale Options

Rodney’s on Broadway in Georgetown is where to go when you want to get gussied up for steaks and fresh seafood served inside a renovated 1840s home. There’s a stunning outdoor patio, which is the place to be on a nice day, but the indoor bar is always full of chatty regulars happy to give you local pointers. 

In Shelbyville, The Bell House serves American fare, including the famous Kentucky Hot Brown (which, I can attest, is a must-order) and iconic spinach artichoke crostini. 

The Classics

KFC is famous around the world, so you obviously can’t visit Shelby County without stopping at Claudia Sanders Dinner House. It was once owned by the Colonel and his wife, and the original fried chicken recipe hasn’t changed since it first opened in the ‘60s. 

Downtown diner Fava’s of Georgetown has been around for a literal century, serving classic comfort food like burgers, pancakes, and a whole case full of pies. You can grab a slice to eat in or bring some back to your accommodations to enjoy later with a nightcap. 

Casual Favorites

Georgetown’s Local Feed occupies a renovated ice house built in 1890 and serves farm-to-table Southern staples: meatloaf, cornbread, deviled eggs, fried chicken, all the appropriate Southern fixins’. While casual dress and catching up among friends is the name of the game here, the food and cocktails could catapult this into the upscale category, no problem. 

You may not have your sights set on beer when visiting the Bourbon Trail, but I implore you to add this stop to your list. Country Boy Brewing started with a few local students’ adventure in Georgetown’s Sister City, Tahara, Japan, and has grown into the town’s beloved brewery. Brews like “Cougar Bait” and “Shotgun Wedding” pair excellently with smashburgers, wings, and smoked meats. The food will knock your socks off, but the “Cliff Jumper” IPA is my current favorite in my beer fridge.  

Unexpected Eats

Dos Mundos in Simpsonville offers Peruvian-Vietnamese fusion you likely won’t find anywhere else. Anything you order is sure to be delicious, but a Pisco Sour or the Summer in Saigon martini (complete with toasted sesame seed oil) and the crispy, lightly fried corn ribs are not to be missed. 

For breakfast, Weathered Oak Farms in Simpsonville is known for its enormous cinnamon rolls, which have become a local legend. Pair one with fresh coffee and shop for locally made pottery while you’re there.

Things to Do Between Distilleries

Horses

You’re in the heart of horse country, after all. Old Friends Farm in Georgetown is a retirement farm for Thoroughbred racehorses—including Kentucky Derby and Preakness winners who now get to live out their days in the lap of luxury. I got to meet the oldest living Derby winner and feed carrots to horses with legendary racing careers, and I’m not exaggerating when I say it felt like being in the presence of celebrities, and I suppose that’s because I was. Even if you’re not a huge racing fan, seeing how loved and cared for these horses are after their sometimes rough racing and breeding lives was very moving. And as a bonus for bourbon drinkers, the farm has partnered with a local distillery to offer signature bottles honoring these equine legends.

At Whispering Woods Riding Stables, I learned how to brush and saddle a horse before riding through the woods. They offer guided rides through wooded hillsides and host events like haunted trails (not on horseback, obviously) around Halloween.

Then, at HorseSensing in Shelby County, see how equine therapy helps veterans transition to civilian life and supports those in recovery from addiction. Small-group tours can be arranged in advance.

The Shopping 

Walking down Shelbyville’s Main Street takes a page out of the American Dream playbook—Shelby Vintage was started by a local kid when he was just 19 years old, offering pre-1990s apparel that’s built such a social media following, people come to town specifically to dig through his inventory. Local milliner Dori Lewis creates 600+ custom pieces a year at The Polkadotted Pineapple, many of which are for the Kentucky Derby. 

The former Science Hill Female Academy, which opened in 1825 based on the radical belief that girls were just as capable as boys in science and math (gasp!), is now the Wakefield-Scearce Galleries. It’s a 35,000-square-foot space that transformed the classrooms, dorms, and courtyards into galleries filled to the brim with English antiques and sterling silver. A pair of sterling mint julep glasses makes an excellent souvenir.

The Unexpected Attractions

Evans Orchard & Cider Mill is a must in fall for apple picking and pumpkin patches, but it’s got charm in other seasons too—seasonal fruits for picking spring through fall, plus a market with local goods and food. Bi-Water Farm & Greenhouse is a massive flower farm that transforms into an autumn paradise come fall: pumpkin patches, bonfires, haunted houses, hayrides.

For history buffs, Ward Hall in Georgetown is one of the nation’s finest examples of Greek Revival architecture still standing. You can walk through the gardens and period rooms, hearing stories about the Ward family—including Sallie, who I’m convinced was America’s original influencer.

And if you’re interested in engineering, Toyota’s largest vehicle manufacturing plant in the world sits right in Georgetown—9 million square feet producing 550,000 vehicles annually. Free tours are offered Tuesday through Friday; make reservations in advance. 

As you’re planning your Bourbon Trail trip, by all means, prioritize the distilleries. Just don’t stop there—leave time in your schedule for the towns themselves and all the lovely Kentucky experiences they offer beyond the bourbon. Happy trails!