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The Bluegrass State lures us in with its rolling green hills, notes of smoky bourbon, and majestic thoroughbred farms. But Kentucky is so much more than its world-renowned Bourbon Trail and picturesque bluegrass-covered horse country. It’s often the little in-between towns that hold all the magic. Come see three of our favorites: Bardstown, Midway, and Maysville.

Bardstown, Kentucky: Small Town, Big Bourbon

Founded in 1780, Bardstown is Kentucky’s second-oldest city and the official Bourbon Capital of the World. Find nine top-notch bourbon distilleries (plus two more set to open by the end of 2022) within 16 miles of charming downtown Bardstown. This vibrant town is home to more than 300 buildings on the National Register of Historic Places, and nearly 200 of those are in the downtown district. Bardstown boasts cozy pubs and taverns, a packed cultural events calendar, as well as fabulous golf and river sports – both whitewater and calm-water. With a population still under 14,000, and so much to explore, Bardstown is chock full of small-town Southern charm that will leave you in the highest of spirits.

bardstown kentucky

Bardstown has been named “The Most Beautiful Small Town in America” by USA Today and Rand McNally. Image: Visit Bardstown


Of course, you cannot skip a visit to one (or more) of the area’s bourbon distilleries like Willett and Barton 1792. Aficionados or those eager to learn and taste, visit Heaven Hill Distilleries Bourbon Heritage Center and Whisky Magazine’s attraction of the year, the Oscar Getz Museum of Whiskey History. Bardstown is also home to the state’s oldest bar, Talbott Tavern, and a slew of locally-owned restaurants and shops. Stop in the Blind Pig Bourbon Marketplace to pick up a rare bottle. Eat, drink and sleep at the luxurious Bourbon Manor Bed & Breakfast.

My Old Kentucky Home

“My Old Kentucky Home” is a historic 19th-century mansion filled with exquisite 200-year-old artifacts, lush gardens, manicured grounds, and rich farmlands. Plus, your tour guides will perform the famous American ballad “My Old Kentucky Home” written by composer Stephen Foster. Image: My Old Kentucky Home

RELATED: The Most Haunted Places in Kentucky

Midway, Kentucky: Small Town, Long Railroad History

Midway is home to some of the world’s top thoroughbred farms settled in the heart of Kentucky’s Bluegrass Region. Built on its intersecting railroad’s fortune, historic Midway was revitalized in the 1970s and ’80s and enjoys a well-deserved reputation as one of Kentucky’s most charming small towns with antiques, crafts, clothes, and culinary hot spots. Several freight trains still make use of the active tracks running through Railroad Street, preserving Midway’s authentic historic atmosphere. Don’t let the town’s population of around 3,000 fool you —  visitors and surrounding locals alike flock to Midway from all over after visiting horse farms and bourbon distilleries. Push it to the top of your road-trip list.

Equus Run Vineyards from above

Equus Run Vineyards is a slice of wine country in bourbon and horse country. Image: Jeff Ashcraft


Stop into the Bluegrass Railroad Museum or explore nature at the expansive and walking-trail-filled Walter Bradley Park. Do a wine tasting at Equus Run Vineyard. Opened in 1998, this winery is where some of Kentucky’s finest wines are crafted. You can take a self-guided stroll through its rolling landscape or book a private tour and tasting. Refuel at the soon-to-be-opened Black Type Company for coffee, wine, books, and gifts …  and discover some fine menswear at Crittenden Rawlings, a shop that will transport you smack dab into the English countryside. After a day of exploring, snag a coveted reservation at Heirloom or Holly Hill Inn for some delicious dishes by two of Kentucky’s best-known chefs.

Weisenburg Mill Midway Kentucky

The Weisenberger Mill has operated at the same site on South Elkhorn Creek since 1865 and still churns out about 70 items you can purchase, like flour, pizza dough, cornmeal, biscuit mix, and more. Image: Ashley Wyatt

RELATED: 3 Kentucky Artists Whose Works You NEED to See

Maysville, Kentucky: A Scenic River Town FILLED with The Arts

Our small-town Kentucky road trip continues northeast — an hour from Lexington — to the charming town of Maysville. Established in 1787, the waterfront town of about 10,000 residents was built from its importance as a trade port on the Ohio River. Today, Maysville preserves its historical backdrop with a heaping dash of undeniable charm, mixed with art-centric cultural outlets and outdoor adventure. A player, of course, in Kentucky’s bourbon production, it’s said that the term “Bourbon Whiskey” was coined in Maysville when barrels were stamped with the phrase before being shipped downriver to New Orleans. The town now lies on the new and popular B-Line: a Bourbon-centric trail of distilleries, taverns, and restaurants that connects Maysville with other small towns in Northern Kentucky.

Pac Cafe Maysville

Paris!? Nope. Maysville! Image: Hannah Lore

Babz Bistro

The coolest backyard vibes can be found at Babz Bistro — a creative bistro-on-wheels concept serving up Southern dishes in a tranquil garden. Image: Babz Bistro


Maysville is rich with arts of all kinds. Visit singer Rosemary Clooney’s former home, let the music move you in the newly restored Washington Opera House (run by the oldest theater group in Kentucky, the Maysville Players), and discover an awe-inspiring collection of 1/12 scale miniatures by master artisans at the Kentucky Gateway Museum Center. Also at the museum, The Old Pogue Experience takes you all the way from the 1791 Whiskey Tax Act Rebellion, into the heyday of bourbon making in the area, through Prohibition, and to the rebirth of an original Kentucky Bourbon. After a packed day of exploring, grab a bite at the European-esque Parc Café, and book a room at the Moon River Bed and Breakfast to be steps from all the action. And, if school is in session, you can pop into College Café for a meal freshly prepared by students of the Maysville Institute of Culinary Arts.

Maysville, KY architecture

Colorful 19th-century row houses and New Orleans-style architecture are two types of homes you’ll see in Maysville. Image: Gardens To Gables

Let’s raise a three-finger-filled glass of bourbon to these three Kentucky small towns — and all the others you will stumble upon along the way!


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