9 Perfect Destinations for a Long Weekend in Kentucky

For a great long-weekend destination in Kentucky, look to the small communities dotted across the state, where many unique experiences await. For example, find bourbon distilleries amid antebellum mansions in Bardstown, and innovative factory tours next to picturesque thoroughbred horse farms in Georgetown. There is always the possibility of adventure in Kentucky, with opportunities for skydiving, hiking majestic waterfall trails, biking amid Red Bud flowers, and a historical tour of Hatfield-McCoy feud sites. With top destinations like Pikeville, Berea, and Slade, learn more about the perfect spots for a long weekend trip in Kentucky.

Pikeville

Most of these towns on this list have interesting histories, but Pikeville might have the most interesting of them all. This town on the Kentucky-Virginia border was one of the territories fought over between the Hatfield and McCoy families. Their feud began during the American Civil War and continued over the decades thanks to escalations over stolen hogs, land, and murder. Here in Pikeville, spend a whole weekend going on a Hatfields and McCoys Feud Tour at sites like the Hog Trial Cabin, Randolph McCoy Homeplace & Well, and the Historic Pike County Courthouse, which put an end to the feud.

By driving 35 minutes outside of the city, one can visit the majestic Breaks Interstate Park, which has a vast 1,600-foot canyon, the largest east of the Mississippi. For lodging during a long weekend stay, Pikeville offers several chain hotels, including Holiday Inn Express and Hampton Inn.

Berea

Known as the Arts and Crafts Capital of Kentucky, Berea is a perfect destination for art lovers. The town is most known for its college, which was the first racially integrated institution of higher learning in Kentucky. The town takes its name from a Greek city praised by Paul in the Bible for its nobility. Berea aims to live up to this reputation through its love of learning and art, which is on display at places like the Kentucky Artisan Center, Berea Arts Council, and Log House Craft Gallery.

Beyond the art, Berea is nestled in the Appalachian Mountains and has several picturesque trails maintained by the Berea College Forest. The best one is the Pinnacles Trail, which leads to scenic overlooks of Berea and the mountain countryside. The best place to stay for a long weekend is at the Historic Boone Tavern Hotel and Restaurant, named after the explorer Daniel Boone.

Slade

For a natural escape, Slade is an underrated Kentucky gem. This rural community sits within the Red River Gorge Geological Area, a canyon with sandstone climbing walls that will challenge even seasoned climbers. Slade's primary attraction is the Natural Bridge State Resort Park, home to a 65-foot-high sandstone bridge spanning 78 feet. This park has several hiking trails descending gorges and through the Natural Bridge Cave, along with canoe rentals for the Mill Creek Lake or the Red River.

For other activities in Slade, visit a quirky zoo at the Kentucky Reptile Zoo, home to multiple venomous snakes and a venom lab. For a long weekend stay, have a peaceful getaway with a dark night sky by renting a cabin from Red River Gorge Cabin Rentals.

Bardstown

Bardstown is one of the most popular towns for a three-day weekend in Kentucky due to its combination of distilleries, museums, and charming architecture. It has the largest concentration of bourbon distilleries in Kentucky, earning it the title of Bourbon Capital of the World. The Heaven Hill Bourbon Experience, Bardstown Bourbon Company, and others provide tours of their facilities along with whiskey samples. Bardstown also has some of the best museums in Kentucky, from the Oscar Getz Museum of Bourbon History to the Old Bardstown Village and Civil War Museum, which has one of the largest collections of Civil War artifacts from the western theatre of the war.

Lastly, Bardstown's architecture inspired Kentucky's state anthem: My Old Kentucky Home. Visit the famed Federal Hill mansion, named after the ballad, at the My Old Kentucky Home State Park. While spending a long weekend here, stay at the Bourbon Manor Bed & Breakfast Inn.

Georgetown

With its bustling car manufacturing industry and fun attractions, Georgetown is the fastest-growing city in Kentucky. However, it still has a small-town vibe that will make any long weekend stay pleasant. The Toyota factory in Georgetown offers a fun tram tour for visitors at the Toyota Kentucky Experience Center, which takes visitors throughout the factory and shows a mint-condition 1988 Camry. For a different kind of horsepower, interact with retired thoroughbred horses from the Kentucky Derby at the Old Friends Retired Thoroughbred Farm.

Another quirky place to see is the Ward Hall, a Greek Revival mansion that was the home of socialite Sallie Ward, who dazzled guests by greeting them in the nude. Georgetown has several chain hotels for a long weekend, including Home2 Suites by Hilton and TownePlace Suites by Marriott.

Elizabethtown

This fun-loving town goes by the nickname Etown, as it is one of the quirkiest towns in the state. Its historic downtown has a Civil War cannonball lodged into one of its buildings, named affectionately The Cannonball. The town received this "gift" from Confederate General John Morgan during his raid in Kentucky. Etown laughs at danger, as can be seen with its Skydive Kentucky business, which offers daring tandem skydiving experiences tens of thousands of feet above ground.

Also in Etown is the Swope's Cars of Yesteryear Museum, owned by the Swope Dealership. This museum has a collection of vehicles from the 1900s to the 1960s. For a long weekend here, book a room downtown at the Holiday Inn.

London

For those traveling with a bike, you will definitely want to stay in London, as this bike-friendly town is called the Cycling Capital of Kentucky. It has all manner of bike shops in town, like Adrenaline Cycles, and fantastic biking trails. The most famous one is the Red Bud Ride, named after the flowers that grow along this rural route, while other mountain biking trails are located at Laurel River Lake. This town played a key role in the early Civil War, as it was the site of one of the earliest battles during the war. At the Camp Wildcat Battlefield, explore old trenches or witness a reenactment of this clash between Confederates and Union soldiers.

London is also right on Boone's Trace Trail, which was trailblazed by Daniel Boone in 1775. Hike this trail at the Levi Jackson Wilderness Road Park. The Red Roof Inn is right off the exit for a long weekend stay here.

Corbin

Corbin is home to several classic Kentucky treasures. The first is the birthplace of KFC (Kentucky Fried Chicken) at the Harland Sanders Cafe & Museum. It was here that Colonel Sanders debuted his secret fried chicken recipe for diners. He would later sell the cafe to start his KFC franchise, but today the town keeps it going as a local curiosity. The other curiosity in town is the Pinball Museum of Corbin, which maintains a collection of playable pinball machines from the 1960s to the present day.

Another Kentucky treasure in Corbin is the natural wonder of Cumberland Falls State Resort Park. This 125-foot-wide and 60-foot-wide waterfall has been called the Niagara of the South, and it is one of the few places in the world where a moonbow (a rainbow caused by the light of the full moon) can occur.

Winchester

For a great trip, you need great food and drink, and Winchester has you covered on both. It is the birthplace of both beer cheese and Ale-8 Ginger Ale. Go on a culinary tour to sample different types of beer cheese with the Beer Cheese Trail, or grab a bottle of Ale-8 from the Ale-8 One factory. Winchester also has a deep heritage going back to the days of the explorer Daniel Boone, who trailblazer through the Bluegrass landscape. See a recreation of his fort at nearby Fort Boonesborough State Park, or explore a Civil War Fort at Boonesboro.

Fun-loving Towns for a Great Weekend

All of these towns are fun-loving in their own way. Winchester is great for snacking on beer cheese while venturing out to historic forts, and Bardstown is perfect for a relaxing day sampling the finest whiskey in the world. Elizabethtown is fun both for history buffs and thrill seekers, while Corbin presents some of the best elements of Kentucky: beautiful natural spots and good food. For those looking to take a long weekend in Kentucky, consider booking a stay at one of these destinations.