Visit These 12 Incredible Charming Small Towns In Kentucky, One For Each Month Of The Year
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Sarah McCosham
Author
Kentucky’s small towns are the very best small towns, and we’re not shy to sing their praises. The Bluegrass State is full of so many winsome little towns, each of which brings something unique to the table. Whether you’re looking for a beach retreat, a historic adventure, a mountain escape, or a country getaway, you’ll sure to find it in Kentucky. As we set our intentions for the upcoming year, make a resolution to visit these 12 charming and best small towns in Kentucky, making each month a new adventure.
January: Harrodsburg
Harrodsburg, KY 40330, USA
New year, a new beginning, and this month's day trip takes us, quite literally, to the beginning of the Bluegrass. Kentucky entered the union in 1792 -- just two states shy of being one of the original 13. Within our storied and historic state, Harrodsburg lays claim to being the oldest town in Kentucky. Founded in 1774, Harrodsburg is the oldest city in Kentucky and the oldest American settlement west of the Allegheny Mountains, earning the town the title "Birthplace of the West." While you're here, be sure to stop by the equally historic Old Owl Tavern, a James Beard Award-winning restaurant that’s part of the Beaumont Inn, a beloved Bluegrass establishment that harkens back to 1845.
Take a look at this video of Harrodsburg by @KentuckyTourism:
Take a look at this video of Harrodsburg by @KentuckyTourism:
February: Rabbit Hash
Rabbit Hash, KY 41091, USA
Looking for "cute towns to visit near me?" We have a big love for Rabbit Hash, Kentucky, so it's only appropriate that this lovely little town is our destination for February. The town's eponymous general store is the heart and soul of the community; a beloved cornerstone since 1831. For a fun overnight getaway, book a night at the Old Hashienda, a rustic inn right in the heart of Rabbit Hash that offers nightly accommodations!
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March: Paducah
Paducah, KY, USA
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 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, especially as temps begin to warm. 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.
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April: Berea
Berea, KY, USA
Another art-loving locale, Berea is an impossibly charming mountain town that's home to a wonderful liberal arts college, thriving arts scene, and lively downtown district. Berea College manages the eponymous Berea College Forest, a 9,000-acre expanse that's home to a network of glorious hikes, including the popular Pinnacles Trail. After a hike, head back to town and enjoy a bite at Apollo Pizza or Hitz BBQ, and then take in some local art.
May: Maysville
Maysville, KY 41056, USA
Marvelous Maysville is peak small-town vibes, with a picture-perfect downtown district offering visitors not only amazing shops and restaurants 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. Our advice? Grab a bike and explore the town on two wheels! This is one of the most charming small towns to visit in Kentucky.
Take a look at this video of Maysville by @earthhealing4090:
Take a look at this video of Maysville by @earthhealing4090:
June: Horse Cave
Horse Cave, KY 42749, USA
Located just 15 minutes from *the* Mammoth Cave, Horse Cave is a charming little town of 2,400 has its own epic underworld, and it's not only Horse Cave's namesake but also its defining feature. Because, you see, the cave for which the city is named is located on the south side of Main Street -- literally smack in the center of town. Operated by the American Cave Conservation Association, public tours are offered year-round, and make for a spectacular *and* cool subterranean adventure, especially as temps begin to heat up above ground!
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July: Grand Rivers
Grand Rivers, KY 42045, USA
Here in the Bluegrass, we're all about lake living, and Grand Rivers embraces these coastal vibes! Grand Rivers is a little lakefront town that's just plain wonderful. A charming lighthouse, fantastic restaurants, and incredible outdoor recreation opportunities make Grand Rivers an amazing place to spend a weekend. While you're there, definitely stay at Lighthouse Landing, a postcard-perfect marina in the heart of town. This is one of the best towns to visit in Kentucky.
Take a look at this video of Grand Rivers by @grandriversky:
Take a look at this video of Grand Rivers by @grandriversky:
August: Greenville
Greenville, KY, USA
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 and makes for a delightful summer day trip. Grab a bite at Aunt M's Cafe and then visit the Big Twigs, an enchanting outdoor art installment at the nearby Lake Malone State Park.
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September: Covington
Covington, KY, USA
Established in 1815, Covington is a historic river town that's home to some of the best taverns, restaurants, hotels, and retailers in the Bluegrass State, including MainStrasse Village. This delightful locale is home to a charming stretch of shops, eateries, and iconic landmarks -- including a Carillon clock tower! -- sure to transport you to the Old World... just in time for Oktoberfest! If you're into German food, you'll be very happy here, with Mainstrasse Village Pub, Otto's, and Wunderbar fan favorites.
October: Cynthiana
Cynthiana, KY 41031, USA
A charming town of around 6,200, Cynthiana is peak "small town" vibes, with a delightful Main Street district, proud local businesses, and scenic beauty. But what this Northern Kentucky town truly prides itself on is its fall foliage -- and it's truly the best in the state. From its cheeky skeletons welcoming visitors downtown in September and October to pretty much *every* house donning harvest decor and Halloween displays, you're sure to fall in love with charming Cynthiana, Kentucky.
November: Danville
Danville, KY, USA
A certified Kentucky Cultural District, Danville is a delightful town that's home to numerous historic landmarks, art galleries, unique museums, and wonderful restaurants. During the winter, Danville is especially charming, with the town adorned in twinkle lights and holiday decor. The perfect place to stop and stay, book a night or two at one of Danville's cozy inns, like Chaplin Hill Bed and Breakfast.
December: Bardstown
Bardstown, KY 40004, USA
There's no better ribbon to tie on this year of day trips in Kentucky than with a visit to Kentucky's very own Christmas Town. While beautiful all year round, Bardstown positively dazzles during the holidays. From mid-November through New Year’s, the Christmas ‘Round Bardstown festival invites guests to come and experience the pure pleasure of the holiday season in Kentucky.
We have a big love for our small towns in Kentucky, and hope you make a point to visit all of the above places this year! Will you be visiting any of the best small towns in Kentucky this coming year? Let us know!
If you plan on taking a road trip anywhere in Kentucky, be sure to check out our Ultimate Road Trip Packing List. And, of course, you’ll need to bring some road trip snacks along!
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More to Explore
Small Towns In Kentucky
Do you have an itinerary for a small-town road trip in Kentucky?
Of course, we do! If you’ve been following OnlyInYourState for a while, you know how much we love road trips. Here’s a sample itinerary for a small towns road trip in Kentucky:
- Stop 1: Danville, KY
- Stop 2: Harrodsburg, KY
- Stop 3: Nicholasville, KY
- Stop 4: Winchester, KY
- Stop 5: Lawrenceville, KY
- Stop 6: Taylorsville, KY
- Stop 7: Bardstown, KY
Check out many more of our best road trips and itineraries in Kentucky.
What is the population of some of the smallest towns in Kentucky?
The Bluegrass State is filled with hundreds of communities, some of which are smaller than others. Between the rural areas and tiny towns around the state, there are plenty of places to find peace and quiet if that’s what you’re after. The following are among the smallest towns in Kentucky along with their populations:
- Wheatcroft, KY: The population as of 2021 was 103.
- California, KY: The population as of 2021 was 80.
- Monterey, K: The population as of 2021 was 111.
- Bremen. KY: The population as of 2021 was 172.
- Thornhill, KY: The population as of 2021 was 182.