9 Picture-Perfect Main Streets In Kentucky

Best known for bluegrass, baseball bats, and horse races, Kentucky is at once widely recognized and often overlooked. Full of charm and ready for a road trip, the state is dotted with small towns where classic main streets create the perfect backdrop for slowing down and soaking in local life. Many of these towns gather around timeless American main streets, just right for exploring, browsing local shops, and grabbing a bite to eat as you wander through town.

In Bardstown, you will find bourbon history and red-brick sidewalks lined with cozy stops, while Pikeville pairs its quaint main street with sweeping Appalachian mountain scenery. Here are nine Kentucky towns that show off some of the state’s most picture-perfect main streets.

Bardstown

If you want to get at the quintessence of Kentucky in a single compact downtown, make a stop in Bardstown. This town has just about everything Kentucky is known for: a picturesque red-brick downtown district, Civil War history…and lots and lots of bourbon. Brewing is Bardstown’s specialty, and you’ll find no end of restaurants and bars on Bardstown’s historic main street that pay tribute to the local specialty. One standout is The Old Talbott Tavern, a landmark that has welcomed travelers and bourbon lovers since the late 1700s.

There’s more than just alcohol in this postcard-pretty downtown, though. Those who prefer their libations to be kid-friendly will enjoy old-timey Hurst Soda Fountain. The long-running Stephen Foster Story is a Broadway-style spectacle honoring one of the area’s most famous sons and a permanent fixture of the local theater scene; non-musical history lessons can easily be had at the Civil War Museum or African-American Heritage Museum downtown.

Danville

The locally-vaunted Birthplace of Kentucky unsurprisingly throws it back to the era of the compact one-horse town with its beautifully-preserved main street. Now a point of local pride, Danville’s leaders have made a point of preserving and enlivening their local downtown. Thanks to their efforts, it’s both a charmingly old-school historic district and a thriving center for the town’s culinary, musical, and artistic life.

But Danville isn’t the only place to look at; it starts with a visit to the GLASS National Art Museum, which displays works by glass artist Stephen Rolfe. Another taste of the local art scene can be had at Danville’s live music venues, like the trendy cocktail club at THE NOOK, where you might catch a spot of Kentucky Bluegrass. From May to October, one notable local favorite is the monthly Downtown Downbeat concert in Weisiger Park. Or enjoy Danville’s two most famous vices in one place at Smoke n’ Bourbon, a cigar-and-bourbon bar paying homage to Danville’s tobacco and distilling industries.

Elizabethtown

Once a critical railroad juncture, Elizabethtown was on the front lines of the American Civil War. These days, it’s a relaxed Southern town of just over 32,000, boasting a lush setting in the heart of Kentucky and a classic main street. Sleepy and slow-paced but vital, the picturesque downtown area of “E Town,” as it’s often called by locals, makes an excellent stop on a road trip or weekend escape.

Like much of Kentucky, Elizabethtown is famous for the bourbon production that goes on right outside of the city, and you can sample the results on Main Street at the Bourbon Barrel Tavern. While Elizabethtown dates back to 1779, Main Street’s delightful 3 Decade Arcade preserves an era a little less far removed from our own with classic 80s arcade games. A little way off Main Street, the excellent Swope’s Cars of Yesteryear Museum delightfully displays antique cars, some of which are impressively rare.

Frankfort

It seems like a misnomer to cite the state capital on a list of charming small-town main streets, but when that capital’s population falls just short of 30,000, it’s easy to see why Kentucky’s biggest little city might be a compelling addition to the list. Frankfort is both a college town and a seat of government, and as such, its lively and picturesque downtown street is one of the state’s most vibrant.

If you’re an architecture fan, starting your trip with a visit to both the old and new State Capitol buildings — both stately edifices in the typical Neoclassical Revival style of early American government buildings — is a must. For a taste of the nearby Bourbon Trail right on Main Street, visit HOC: A Bourbon Library for a tasting and sample local bourbons you won’t find anywhere else. If you’re not into bourbon, enjoy browsing the shelves at Poor Richard’s bookshop before a lively meal at Bourbon On Main.

Henderson

Henderson prides itself on natural beauty: not only does it get a boost from its lovely setting along the Ohio River, but it was the one-time residence of the renowned naturalist and bird illustrator John James Audubon. But on the man-made side of things, Henderson is an agreeable, slow-paced town with most of its draws clustered around a wide, pleasant main street.

Just off of Main Street along the riverfront, you’ll find Audubon Mill Park. Visit this local landmark to see where the famous naturalist once lived. If you’re in town in August, that same park hosts the Bluegrass in the Park Folklife Festival, so stop by to listen to the state’s home-grown genre of folk music. Or, if you’d rather learn a little while you wander, Historic Henderson Downtown Walking Tours offer context on the town’s fascinating history from local experts. Follow up your sightseeing with a meal at the upscale Cap & Cork, a bourbon-focused spot offering cocktails, fine dining, and a cigar lounge.

Midway

Ask any American what comes to mind when they think of Kentucky, and you can bet good money that most will answer, “horses.” The state gets most of its media coverage during the world-famous Kentucky Derby, and although you may not have heard of the town of Midway, it contributes to that proud tradition: the town is locally renowned for its thoroughbred horse farms. Though Midway’s main street is a lovely town centerpiece, it’s only part of the story.

For those who’d like to dive into the area’s surprisingly storied history, the Bluegrass Railroad Museum chronicles its past as a railway boomtown. (It was the first town in Kentucky to be founded solely for the purpose of railroad construction.) The historic Weisenberger Mill still sells locally-milled products in a facility operated since 1865. And if you’d prefer a boozy diversion, fear not: with several distilleries open for tours, Midway is a stop on the Kentucky Bourbon Trail.

Paducah

A humble Kentucky town of 27,000 might not seem like a likely pick for a UNESCO Creative City, but Paducah is full of surprises. It all starts with one of the state’s most gorgeous main streets, as classic and picturesque as you could hope for, and continues at the National Quilt Museum. Even if you're not normally interested in textile art, plan on a stop: it's an excellent introduction to a local craft and one of Kentucky's finest museums.

Out in the streets of Paducah, keep an eye out for the vintage-style murals depicting scenes from local life and history on the town’s floodwalls. And if you’re not into the whole Creative City thing, worry not: located at the confluence of the Ohio and Tennessee Rivers, there are plenty of opportunities for water sports, cycling, and birdwatching in Paducah.

Pikeville

It’s one thing to build and maintain a pretty main street. It’s entirely another to be blessed with the natural setting to make that main street unforgettable. And Pikeville, situated in the Appalachian Mountains, achieves both. While many of Kentucky’s main streets stand out for their long and colorful histories, Pikeville is a nature lover’s kind of place.

Sure, there’s history to be had: the storied Hatfield-McCoy feud played out right here in Pikeville. But it’s out in the mountains that you really get to know Pikeville. Take a horseback ride with a local outfitter, hike up to the overlook at Bob Amos Park for views of the lush green hills, or take the self-guided Hatfields & McCoys Feud Historic Driving Tour. Oh, and a pro tip: Pikeville’s mountain scenery is at its most impressive in autumn, when the fall colors are out in full force!

Shelbyville

As the “Saddlebred Capital of the World,” Shelbyville is yet another example of the deep importance of all things equine in Kentucky culture. Boasting one of the state’s nicest main streets, the greater Shelbyville area is also home to no less than seven horse farms and the famous annual Shelbyville Horse Show.

But there’s also much to see on Main Street itself. The Downtown Sculpture Walk guides visitors to eight locally designed art installations and provides a quirky introduction to the town’s compact downtown. Stop by the Science Hill School for a lesson in local history: now a museum, it was once one of the premier girls’ prep schools in the U.S. And if all that exploring is making you hungry, a meal or afternoon tea at the Bell House Restaurant - a 1902 house given new life as a charming café - is a perfect stop.

Final Thoughts

If you’re craving a slice of small-town America in a picturesque setting, consider making your way to the often-overlooked state of Kentucky. Whether you’re looking for artisan bourbon from the source, colorful local histories to learn, or just a charming place to shop and eat while enjoying the slow Southern life, there’s a Kentucky town or several calling your name. There’s no better place to slip into the rhythm of a mellower life: find a café with a lovely patio, order that Kentucky Hot Brown sandwich, and watch life go on by.