Sure, the distilleries are the main event. But one of the best parts of exploring Bourbon Country is everything that happens between the distilleries.

The small-town coffee shops. The local boutiques. The historic storefronts. The conversations with shop owners who have probably been there longer than most of the bourbon brands you’ve heard of.

While Kentucky is home to some world-famous distilleries, it’s also home to some pretty incredible Main Streets. And if you’re touring with Kentucky Bourbon Boys, there’s a good chance you’ll pass through a few of them along the way!

Here are three of our favorites:

Bardstown: The Bourbon Capital’s Main Street

If Bourbon Country had a postcard, Bardstown would probably be on it.

Known as the Bourbon Capital of the World, Bardstown blends bourbon heritage, Kentucky history, and small-town charm better than just about anywhere else in the state. What makes Bardstown special isn’t just the bourbon – it’s the energy.

From the Kentucky Bourbon Festival to the dozens of community events and celebrations held throughout the year, there’s almost always something happening downtown. And with the historic courthouse square serving as the heart of downtown and My Old Kentucky Home State Park located just minutes away, Bardstown feels like a place where Kentucky’s history and culture are still very much alive.

Fun Fact: In 2023, Travel + Leisure named Bardstown one of America’s Most Beautiful Small Towns, and honestly, we’re not arguing. If you’re touring along the Bourbon Trail, Bardstown is one of those places worth taking a little extra time to explore!

Midway: Kentucky’s Comeback Kid

Nestled between Lexington and Frankfort, Midway feels like something straight out of a movie – and that’s because it kind of is.

This charming town served as a filming location for the 2019 Hallmark movie A Christmas Wish. Once you stroll down Main Street, you’ll understand why.

The railroad tracks still run directly through the center of town, creating a backdrop that feels both historic and uniquely Kentucky. But that’s not all that’s inspiring about this quaint but mighty town.

After a devastating fire destroyed much of downtown in 1915 and rail travel later declined, Midway faced a number of significant setbacks. Fortunately, that’s not where the story ends.

Local business owners and community leaders helped breathe new life into downtown, transforming it into the charming destination visitors enjoy today. Now you’ll find locally owned boutiques, restaurants, galleries, and historic buildings lining the same streets that helped put Midway on the map nearly 200 years ago.

Fun Fact: Midway was the first town in Kentucky established by a railroad and got its name because it quite literally sits midway between Lexington and Frankfort.

LaGrange: Kentucky’s Kindness Capital

Located just outside Louisville, close to Kentucky Artisan Distillery, LaGrange is one of those towns that’s easy to underestimate.

At first glance, it’s your typical charming downtown, but spend a little time wandering, and you’ll quickly understand why visitors often end up staying longer than planned.

Known as the “Kindness Capital of Kentucky,” LaGrange hosts weekly farmers markets, its popular Trackside Tunes summer concert series, and seasonal festivals throughout the year. It’s a small town with a big personality.

Fun Fact: LaGrange is one of only a handful of communities in the United States where active freight trains still run directly through the center of downtown streets. (Don’t worry, the locals are used to it.) In fact, it’s become one of the town’s most beloved attractions.

Bourbon Country Is More Than Distilleries

Don’t get us wrong. We love the distilleries. But some of the best memories from a bourbon trip happen when you’re wandering a Main Street, finding a great local restaurant, or discovering a shop you weren’t planning to stop in.

Bardstown, Midway, and LaGrange each offer a different glimpse into Kentucky’s character, and all three remind us why Bourbon Country is about so much more than what’s in the glass.

When you’re planning your next Bourbon Trail adventure, don’t just think about the distilleries. Leave a little room for the towns in between. You might be surprised by what you find.