If you want a true taste of the Bluegrass, just visit one of our many Main Streets. Kentucky’s downtowns are simply the best; full of history, winsome beauty, and the most charming, delightful local shops and businesses. There’s nothing quite like wandering through a bustling downtown district in the Bluegrass, perusing locally owned shops, stopping into family-owned restaurants, and checking out some of the best small town shopping in Kentucky! These seven small towns in Kentucky have the most charming downtowns; visit and you’re sure to fall in love — and make some amazing memories, too!

1. Paducah
Paducah, KY, USA
Paducah Creative City/Facebook
Located in the southwestern end of the state, Paducah is a proud river city that’s big in natural beauty and the arts. This well-rounded Kentucky gem has a thriving creative community and boasts attractions and experiences that you just won’t find anywhere else. The downtown is charming and walkable, and your chances of stumbling upon live music or a festival here are high! Stroll through the vibrant town square or head to Paducah's Historic Riverfront, a favorite spot for folks to come and enjoy the stunning waterfront scenery.
2. Bowling Green
Bowling Green, KY, USA
Visit BGKY/Facebook
With a population of 70,000, Bowling Green is by no means small; however, there is a charming, small-town vibe here that’s impossible to miss. You’ll find friendly faces, fascinating history, plenty of green space, and all sorts of unique attractions in Bowling Green's vibrant downtown district. The historic Fountain Square Park is its crown jewel, and it's a beautiful spot to sit and watch the world go by. While you're there, definitely try the Kentucky Bourbon Filet from Montana Grille!
3. Elizabethtown
Elizabethtown, KY, USA
Elizabethtown Tourism/Facebook
The lovely Elizabethtown is a hidden gem; this winsome town is perfectly located amongst some of the state's most popular attractions, but it also stands as a destination in and of itself. The historic downtown district is the town's centerpiece and has an abundance of unique shops, restaurants, and plenty of history. During the summer months, you can take a guided walking tour around town and learn about Elizabethtown's past. In the off-season, you can download an app and take your own tour -- just make sure to visit all of the hidden gems and historical markers!

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4. LaGrange
La Grange, KY, USA
Morgan/Wikimedia Commons
La Grange is an all-around small-town superstar that offers visitors a fun and wholesome Bluegrass experience. Most notably, LaGrange is known as the only town in America that has an active train running along its Main Street. While it's one of the most unique features of the town and the first thing you may notice, there's so much more to see and do in this historic town. From historic demonstrations to an abundance of charming shops and local restaurants, LaGrange is a very walkable small town and the perfect place to wander and explore!
5. Maysville
Maysville, KY 41056, USA
David Wilson/Flickr
Maysville is peak small-town vibes, with a picture-perfect downtown district offering visitors not only amazing shops and eateries but also a crash course in Bluegrass history. Truly -- if you are curious about history, you'll find it around every corner in Maysville, with numerous Underground Railroad sites, the National Underground Railroad Museum, the Colonel Charles Young Birthplace Cabin, the Mays Lick Rosenwald School, and, just outside town, the oldest covered bridge in Kentucky.
6. Greenville
Greenville, KY, USA
Greenville Tourism Commission/Facebook
Founded in 1799, Greenville is an idyllic little town located in western Kentucky’s rolling blue hills. Renowned for its family-friendly festivals, historic downtown, and Southern hospitality, Greenville is about as charming as it gets. Experience the splendor of this small Kentucky town by booking a night at The Wickliffe House, a historic inn located right in Greenville's bustling downtown district!
7. Bardstown
Bardstown, KY 40004, USA
Visit Bardstown/Facebook
Of course, we simply cannot talk about charming downtowns in Kentucky without including Bardstown. This lovely locale is full of top-rate distilleries (the town is known as the bourbon capital of the world, after all), historic buildings (like My Old Kentucky Home), and beguiling beauty. Experience Bardstown to the fullest by spending a night at the Bourbon Manor B&B. Just be warned: once you visit Bardstown, you might never want to leave!

What are your favorite downtowns in Kentucky to visit? Your top picks for the best small town shopping in Kentucky? If we missed your favorite Main Street in the Bluegrass State, be sure to nominate it and tell us why it’s so special!

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best small town shopping in kentucky

Sarah M. | September 16, 2022

What are some locally owned stores for shopping in Kentucky?

There's nothing like supporting a local business, and the Bluegrass is full of #KentuckyProud establishments that celebrate the makers, growers, and entrepreneurs in our fine state! Bourbon Barrel Foods is a shop in Louisville, Kentucky, that produces a collection of all-natural, award-winning foods that embrace the history and proud culture of Kentucky's Bourbon Country. This isn't your standard spirits shop, however. With a tagline of "Eat Your Bourbon," this place takes bourbon to another level of culinary mastery. All of the items sold in the store are handcrafted in Louisville, Kentucky, using reclaimed (Kentucky) distillery barrels for smoking and aging, two processes that impart an unrivaled depth of flavor! Bourbon Barrel Foods is well-known for its bourbon-spiked sauces. From classic barbecue to ponzu and soy sauce, bourbon has a place in cuisine from all around the globe. Talk about the ultimate Kentucky-owned shop for Bluegrass bourbon enthusiasts!

Another spot for shopping in Kentucky that we love is Earth to Kentucky, a bootleg toy store that sells one-of-a-kind toys, collectibles, vintage throwbacks, and more. You're also sure to find those hard-to-find action figures and rare toys needed to complete your personal collection. What a fun spot for toy collectors!

Finally, we'd be remiss not to mention Butchertown Market in our praise of all things "shopping local" in Kentucky. This one-of-a-kind shopping market in Louisville has it all: antiques, locally made wares, Bourbon Barrel Foods swag (see above!), and so much more, all wrapped in an irresistibly charming package in one of the city's most historic neighborhoods.

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