The Best Weekend Getaways in Kentucky

From a romantic weekend in Somerset to an outdoor adventure in Mammoth Cave National Park, Jerry has the inside scoop on the best weekend getaways in Kentucky!
Written by Patrick Price
Reviewed by Kathleen Flear
Updated on Sep 27, 2022
If you’re looking for a minivacation in
or an impromptu adventure in
, Kentucky is the perfect playground for a quick two-day getaway.  
All too often, the weekend goes by in a flash. But what if, Instead of an empty blur of Netflix and naps, you make this weekend one that you’ll remember for years? Maybe it’s time to take a weekend getaway to somewhere in
and put some miles between you and Monday morning! 
The only question is, where do you go? 
Don’t worry.
, the
car insurance
super app
, has got you covered! Whether you’ve been needing a romantic weekend with that special someone, a fun trip for the whole family, or just a quiet place to enjoy nature, Jerry has the field guide to the fun that you’ll need! 
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The best weekend getaways for couples in Kentucky


Stay at:
Relaxing Lakefront Getaway
via Vrbo (rooms from $178/night)
Lost Lodge Resort
(rooms from $109/night)
Whether you’re pining for an unparalleled adventure in nature or a quiet getaway in the downtown area,
has everything needed for an unforgettable weekend with your significant other. 
Take on the untamed beauty of
Cumberland Falls State Resort Park
, just a couple of hours north of town. There, you can get in touch with nature while hiking the
Anvil Branch Trail
or share a romantic
horseback ride
through the woods. 
For those couples who prefer a calmer atmosphere, you can spend a cozy afternoon exploring the
charming downtown
of Somerset. Stop in at
Lake Cumberland Farmers Market
The Mole Hole & Tipsy Toad
to shop for unique souvenirs of your weekend. 
Enjoy a fun tour of the town’s vibrant arts scene at the
Carnegie Community Arts Center
Wandering Elm Photography
—or take in a show at the
Flashback Theatre Co
. After that, grab a finely crafted drink together at
Jarfly Brewing Co


Stay at:
Boone Tavern Hotel
(from $115/night)
Pinnacle View Inn - Berea
(from $131/night)
Whisk your special someone away to an enchanted weekend in the breathtaking, forest-clad foothills near the town of
This charming little town is well known as the folk arts and crafts capital of Kentucky. If you’re looking for a weekend getaway immersed in artistic expression and events, Berea is the place for you. Enjoy the art festivals, historic restaurants, and vintage architecture for which the town is known—not to mention the sprawling natural beauty that surrounds it!
To satiate your hunger for unique artistic expression, take your significant other to the
Berea Arts Fest
or the
Berea Craft Festival
. You can also check out the
Artisan Village District
for a veritable buffet of unique artistic sights. 
Go nick-knack hunting at
Todd's Antique Mall
. Then, enjoy a fine meal at the intimate
Historic Boone Tavern Hotel and Restaurant
The next morning, after a delicious breakfast at
La Crepe Bakery & Cafe
, venture out for some one-on-one time alone in nature as your
hike The Pinnacles
–the #1 rated hiking trail in Kentucky!  
Pro tip Berea is a wonderful little town to spend a weekend—which is a well-known fact. Expect there to be a lot of other visitors with the same idea as you. Book any reservations well in advance to make sure you get a spot. 

The best weekend getaways for families in Kentucky


Stay at:
Aloft Newport on the Levee
(rooms from $139/night) 
Hampton Inn & Suites Newport
(rooms from $220/night)
is the best place for a family-friendly weekend getaway in Kentucky. This city is absolutely packed with educational activities and river-based fun
Start the weekend with some interactive and engaging learning for the kids at the renowned
Newport Aquarium
. Then, step back in time at the kid-friendly
Big Bone Lick State Historic Site
where you can learn about the exciting history of American paleontology! 
Stop for a quick lunch at
where you can enjoy a rich german-heritage theme, great food, and (for the grown-ups) some cool refreshments! Digest all that good food while relaxing at the scenic
Bridgeview Box Park
, then take the kids for a spin on
Carol Ann's Carousel
Wind down the evening by taking the whole family on a once-in-a-lifetime ride over the river courtesy of
BB Riverboats


Stay at:
The Galt House Hotel
(rooms from $179/night)
The Brown Hotel
(rooms from $265/night)
For a whirlwind weekend, book a trip to vibrant and bustling
. Whether you’re a family of sports lovers, a band of art enthusiasts, or just a gang of good old-fashioned fun lovers, there’s something for you in Louisville. 
Step into an immersive vision of our nation’s sporting tradition at the
Louisville Slugger Museum & Factory
—watch these iconic bats crafted right before your eyes and see how legends are made! Or learn about a boxing hero at the
Muhammad Ali Center
For slightly more high-brow fun, take the family to
The Speed Art Museum
or hop across the river into
and visit the
Cincinnati Art Museum
If sports and arts aren’t appealing to your clan, don’t worry—Louisville is bursting with endless attractions for those that just love to have a good time! At
Malibu Jack’s
, the whole gang can enjoy go-karts, laser tag, mini-golf, and the arcade–not to mention the great food! Or, take pay a visit to
, a massive play center that’s great for kids of all ages! 

The best weekend getaways for horse racing enthusiasts in Kentucky

Churchill Downs, Lousiville 

Stay at:
The Churchill Backside
(rooms from $450/night)
Cozy Getaway AriBnB
(rooms from $110/night)
Kentucky is perhaps the most iconic location in the world for horse racing. Get right to the heart of the action by planning a weekend of fun centered around the legendary racetrack
Churchill Downs
Of course, there are exciting
events and races
at The Downs all year, but the main attraction is the
Kentucky Derby
. Every year, The Downs celebrates the most famous horse racing event of all time with an entire week of festivities. Collectively referred to as Derby Week, this extravaganza is a must-see event for anyone who enjoys spending time at the track. 


Stay at:
21c Museum Hotel Lexington
(rooms from $199/night)
Staybridge Suites Lexington
(rooms from $110/night)
If there’s one place that can compete with the appeal of Churchill Downs for horse-lovers, it’s
—the Horse Capital of the World.
Visit the famed
Kentucky Horse Park
for some must-see horseshows and events and witness some of the best riders and the best horses in the world. You can even visit the barns—which are open to the public—and spend some time with the horses. 
If you want to learn more about these four-legged marvels, go to the
International Museum of the Horse
. Then, see where the greatest racehorses in the world are trained at
—the heart and soul of Lexington’s racing culture. 
Take a break from the tracks and visit the
Raven Run Nature Sanctuary
or the
Waveland State Historic Site
. Take in some artistic culture at
Institute 193
or just kick back with a cold drink at
Alltech’s Lexington Brewing & Distilling Co
Pro Tip Lexington is a dynamic town full of rich history and vibrant culture. There’s a lot to see there besides the horses. Make sure you schedule some time to explore the city! 

The best weekend getaways for foodies and adult beverage aficionados in Kentucky


Stay at:
Jailer’s Inn
(rooms from $148/night)
Bourbon Manor Bed and Breakfast
(rooms from $206/night)
Anyone who appreciates a finely distilled drink is familiar with the famous bourbon whiskeys produced in Kentucky. No place in The Bluegrass State exemplifies this tradition more than
—the Bourbon Capital of the World
If you consider yourself a connoisseur of fine liquor, then visiting this idyllic little town is a pilgrimage you’ll need to make at least once. Bardstown is home to 11 of the most highly regarded distilleries in the world. You can sample the whiskey and take tours of
Barton Distillery
Heaven Hill Distillery
, or
—just to name a few!
To learn more about the history of bourbon in Bardstown, visit the
Oscar Getz Museum of Whiskey
. If you are there in mid-September, you also can catch the
Kentucky Bourbon Festival
—a weekend-long celebration of the town’s rich bourbon history!  
If alcohol isn’t really your thing, don’t worry—Bardstown has plenty more to offer! In fact, it was named the Most Beautiful Small Town in America. Take in some of the beauty by strolling through
Bernheim Arboretum And Research Forest
or the ornate architecture of the
Basilica of St. Joseph Proto-Cathedral
. Then stop by the
Civil War Museum
to learn about our nation’s most turbulent chapter. 


Stay at:
Murray Inn and Art Gallery
(rooms from $82/night)
America's Paradise Resort
(rooms from $127/night)
If you’re looking for a foodie’s paradise, look no further than
. Don’t let its small size fool you—this beautiful little city may have small-town charm, but it’s got big-city taste buds! 
Start your weekend-long food binge with an authentic Kentucky breakfast at
Hungry Bear Pancake and Bar-B-Q House
. This hole-in-the-wall local favorite is well hidden but well worth the hunt. 
Give yourself some time to digest by lounging at
The Arboretum
—a gorgeous outdoor recreation area on the grounds of Murray State University. Then head to lunch at
Los Portales
which serves the most mouthwatering authentic Mexican cuisine you’re likely to find. 
Take a stroll through the rustic downtown
to Murray Court Square and maybe stop in a shop or two. Prep your pallet and your stomach for dinner with an afternoon drink at
Tap 216
Next, it’s on to the main event! Experience a southern seafood culinary explosion that you’ll never forget at
The Keg
! Or, for something a bit more refined, stop by
Jasmine Thai & Sushi Grill
Then, if you’ve had your fill, take a walk through Central Park and maybe catch a performance by the
Playhouse in the Park

The best outdoor weekend getaways in Kentucky

Mammoth Cave National Park

Stay at:
Lodge at Mammoth Cave
(rooms from #93/night)
Historic Wigwam Village No. 2
(from $121/night)
For outdoor adventure in Kentucky, you can’t beat
Mammoth Cave National Park
—a sprawling wonderland rich with human history, prehistory, beautiful woodlands, and the world’s longest known cave system
You’ll find plenty to do in the park. Obviously, you’ll want to start your vacation off with a
tour of the caves
. After that, though, you can busy yourself by
, or
horseback riding
through the park's
many trails
If you prefer the sea-faring lifestyle, you can head to one of the park’s
access points to the Green and Nolin Rivers
. From there you can shove off and start a floating adventure of
canoeing, kayaking, or boating
Change things up with a gorgeous yet ghoulish tour of the time-weathered
historic churches and cemeteries
in Mammoth Cave National Park. 

Lake Cumberland State Resort Park

Stay at:
Lake Cumberland Lodge or Cottage
(cabins start at $175/night)
Lake Cumberland Camping sights
(campground reservations start at $24/night)
Spend a weekend surrounded by tranquility and natural beauty when you plan your Kentucky getaway for
Lake Cumberland State Resort Park
. This gorgeous woodland lake may look wild at first glance, but it is well-equipped with every imaginable comfort and convenience–while not sacrificing the rugged outdoor atmosphere. 
Lake Cumberland State Resort Park is a popular spot for
recreational fishing
and you’ll find great waters for catching largemouth bass, smallmouth bass, white bass, Kentucky bass, bluegill, crappie, rockfish, and walleye. You can even pay a visit to the
Wolf Creek National Fish Hatchery
and learn a little about the fish that you catch! 
You can, of course, also enjoy
, boating,
, swimming, and camping. You can also relax on one of the park’s
miniature golf courses
, disc golf courses, playgrounds, picnicking areas, and tennis courts
Pro Tip Lake Cumberland State Resort Park takes preventing the spread of COVID-19 seriously. Make sure that you’ve familiarized yourself with their
safety recommendations
before visiting.  

The best weekend getaways for history buffs in Kentucky


Stay at:
Beaumont Inn
(rooms from $165/night)
Shaker Village of Pleasant Hill
(rooms from $112/night)
Get in touch with the past with a weekend getaway to
—the oldest city in Kentucky and one brimming with history! 
Start things off with a breakfast at the
Beaumont Inn Dining Room
which has been serving guests for 102 years! Then, check out the historic farm/village and landmark destination at the
Shaker Village of Pleasant Hill
—you also can rent a room at either of these two sights! 
Get a taste of what life was like in Kentucky back in the day at the
Old Fort Harrod State Park
—a shockingly well preserved historical sight. Have fun like a pioneer in
Devine's Corn Maze & Pumpkin Patch
—just don’t get lost! 
Be sure to take a piece of the history home with you when you shop at
Back Porch Treasures Craft & Antique Mall
Wrap things up with a catered voyage on an actual working steamer ship with
Dixie Belle Riverboat Rides


Stay at:
The 1857 Hotel
(rooms from $140/night)
Drury Inn & Suites Paducah
(rooms from $112/night)
Enjoy a weekend drenched in the past—and in great quilts—when you visit
. This Kentucky town is known for two things: being rich in history and being the quilt capital of America
Take a tour through The
National Quilt Museum
to learn about this town's unique quilting history. For a more serious glimpse into the past, head over to the
Lloyd Tilghman House and Civil War Museum
and the
William Clark Market House Museum
Go for a stroll along the
historic riverfront
and drink in the atmosphere. Then, take a break from the past and get to know the contemporary culture of Paducah at the
Yeiser Art Center
Later in the afternoon, you can get a stiff sip of history at The
Moonshine Company
and learn about the history of whiskey production during prohibition! 
If you’re looking for something to eat as you explore Paducah’s history, stop in at
The Freight House
Doe's Eat Place

The best cheap weekend getaways in Kentucky 

Falling Rock Park

Stay at:
Best Western Ashbury Inn
(rooms from $47/night)
Comfort Inn & Suites
(rooms from $82/night)
One great way to stick to your budget but still sneak away for a fun weekend is to spend a couple of days at
Falling Rock Park
. For only $35, you can buy admittance to the natural water park and have a whole day of fun! 
Float along the lake in an innertube or jump off the high rocks into some of the clearest water you’ll ever see! For an extra fee, you can even
go diving
in the park! 
Enjoy the sun, the water, and the boating opportunities! When you’re ready to dry off, head over to the nearby town of
La Grange
—a charming little slice of Americana. 

My Old Kentucky Dinner Train

Stay at: On the train! (rooms from $81/ride)
Take a ride through scenic Kentucky with
My Old Kentucky Dinner Train
! Take in all the beauty of the countryside while enjoying good food and good bourbon! Ride packages range from $81 - $127 per person and include everything you’ll need for a fun weekend!

Why you need good car insurance (and how you can save on the best!)

As you plan your weekend getaway to
, there’s one thing you can’t forget–making sure you’re covered with dependable
car insurance
! The last thing you need while planning a mini-vacation is to be underinsured or stuck paying way too much for coverage.
can help with that! 
Jerry is an expert at saving you time and money! And don’t worry, Jerry isn’t an insurance company—it’s a free app that helps you find the best deals on car insurance and get signed up for them in just a few minutes! 
Even if you already have coverage, the odds are good that Jerry can find your equal or better coverage for a much lower rate. In fact, drivers who use Jerry save an average of $887 a year.
was helpful every step of the way. They saved me over $100 a month for insurance in Kentucky.” —Jim F.
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