10 Of The Friendliest Towns In Kentucky

Kentucky has always had a knack for being a little unexpected. Sitting between North and South, bordered by mountains, rivers, hills, and hollows, it blends long-standing traditions like bourbon distilling, beer cheese, and horse raising with unusual attractions and local customs that feel very much its own. Across the state, small towns welcome visitors with stories, festivals, and traditions that do not always fit neatly into a brochure. These communities offer good food, local music, outdoor activities, and the kind of character that comes from people doing things... let's say... their own way.

Georgetown

Georgetown is the fastest‑growing city in Kentucky, with an estimated 40,600 people living there as of 2026, but it still keeps a small‑town feeling as it grows. This is especially true because it is a short distance from Kentucky’s second‑largest city, Lexington, leaving Georgetown feeling positively village‑like in comparison. One of the major drivers of growth in the town is the Toyota plant, which provides employment to thousands of people in the area, and visitors can take a tram tour of the factory with the Toyota Experience. Georgetown has a sister‑city relationship with Tahara, Japan, that has also helped create active cultural and business ties with Asia.

Another unusual feature of the community is that it is where many retired horses from the Kentucky Derby come to spend their twilight years. You can meet these horses at Old Friends Thoroughbred Retirement Farm. The community gathers to honor horses at the Festival of the Horse held annually in September. You might also enjoy visiting the 1853 Greek Revival plantation Ward Hall, which was the home of a fun‑loving socialite who reportedly loved to shock guests with her outrageous behavior.

Paducah

Paducah stands out because creativity is woven into daily life. The town holds a UNESCO designation as a Creative City of Crafts and Folk Art, and that title is not just ceremonial. Along the Ohio River floodwall, large murals tell stories of Paducah’s past in bold, detailed scenes. The National Quilt Museum turns a traditional craft into something surprising, with modern designs and hands-on workshops. Local theater also plays a big role here. The Market House Theatre and the Clemens Fine Arts Center host plays, classes, and seasonal events, including popular fall ghost tours.

Berea

Berea’s identity is shaped by education, craftsmanship, and a strong sense of purpose. Berea College made history as the first interracial and coeducational college in the South. Even after segregation laws were imposed, the college continued to uphold its founding principles, which can still be seen at historic sites like Lincoln Hall, completed in 1887. The town is equally known for its commitment to folk arts and crafts. The Kentucky Artisan Center displays and sells work by regional artists, including pottery, paintings, and handmade goods. Every July, the Berea Craft Festival fills the town with artists and visitors. Many of these works draw inspiration from the surrounding Appalachian landscape, which can be explored on foot along the Pinnacles Trail in the Berea College Forest.

Pikeville

Pikeville’s history includes one of the most infamous feuds in American folklore. The Hatfield and McCoy Feud began with a dispute over land and the ownership of a hog and escalated into years of violence. Today, visitors can learn about this chapter through the Hatfield & McCoy Feud Tour, which stops at sites such as the Hog Trial Cabin, the Randolph McCoy Homeplace and Well, and the Pike County Courthouse. Modern Pikeville balances that dark past with a strong arts and performance scene. Live events at the Appalachian Wireless Arena and the Artists Collaborative Theatre Inc. bring people together year-round. Each April, Hillbilly Days draws large crowds for music, food, and charity events that reflect the region’s sense of humor and resilience.

London

London has carved out an identity around two things that do not usually go together: bicycles and fried chicken. Known as the Cycling Capital of Kentucky, the town supports riders with shops, routes, and events like the downtown Redbud Ride, named for the flowering trees along nearby roads. Trails around Laurel River Lake add options for mountain biking. In September, attention shifts to the World Chicken Festival, where cooks use what is billed as the world’s largest stainless steel skillet. History also has a place here. Visitors can explore the Camp Wildcat Battleground with reenactors who enjoy answering questions, or walk Boone’s Trace at Levi Jackson Wilderness Road Park, which follows early frontier paths tied to Daniel Boone.

Corbin

Corbin’s story includes fried chicken, waterfalls, and a festival named by spelling the town backward. Colonel Harland Sanders first served his fried chicken here, a legacy preserved at the Harland Sanders Cafe and Museum downtown. Nearby Cumberland Falls State Resort Park draws visitors to a broad waterfall carved into the Cumberland River gorge. Hiking trails wind through the park, and during certain full-moon nights, conditions sometimes allow views of a moonbow created by reflected moonlight. In August, the town celebrates with the NIBROC festival, featuring crafts, food, and community events. Visitors with a taste for nostalgia can also stop by the Pinball Museum of Corbin, where classic machines still light up and clang.

Winchester

Winchester has a habit of turning everyday food and drink into local traditions. The town is the birthplace of Ale-8-One, a ginger-citrus soft drink introduced in the 1920s that is still produced locally. The Ale-8-One factory offers tours and merchandise. Winchester also lays claim to beer cheese, a regional favorite celebrated through the Beer Cheese Trail and the Beer Cheese Festival each June. Nearby Fort Boonesborough State Park adds another layer, offering insight into frontier life and Civil War history connected to Daniel Boone’s early exploration of Kentucky. The mix of snacks, stories, and local pride gives Winchester a personality that is easy to remember.

Elizabethtown

Elizabethtown, often called “E-town,” balances history with a fondness for odd details. With around 31,000 residents in 2020, it offers plenty to explore without losing its neighborly feel. Downtown features a cannonball embedded in a building, which local tradition links to a Civil War skirmish. Nearby, Swope’s Cars of Yesteryear Museum houses a large collection of vintage vehicles that surprises first-time visitors. Fall brings busy weekends with the Highland Festivals and the Heartland Harvest Festival, complete with vendors, activities for kids, and a 5K race. For something less grounded, Skydive Kentucky nearby offers tandem jumps for those ready to try something memorable.

Bardstown

Bardstown leans into its reputation as a bourbon town and does so enthusiastically. Distilleries like Heaven Hill’s Bourbon Heritage Center offer tours and tastings, while smaller operations add their own twists. The Oscar Getz Museum of Bourbon History, located in Spalding Hall, and the Kentucky Bourbon Festival each September keep the focus on tradition and storytelling. Beyond spirits, Bardstown also offers museums covering Civil War history and regional life. Just south of town, Bernheim Arboretum and Research Forest features walking paths and oversized wooden troll sculptures made from reclaimed materials, adding an unexpected element to a walk in the woods.

La Grange

La Grange is proud of doing at least one thing differently than almost anywhere else. A mainline railroad still runs straight through its U.S. Main Street, with trains passing through downtown multiple times a day. The La Grange Railroad Museum explains how this shaped the town’s development and occasionally hosts excursions or dinner trains. Families gather at the Sauerbeck Family Drive-In to watch movies, keeping a long-running tradition alive. During the summer months, FRP LaGrange Quarry opens as a swimming area, giving visitors the unusual chance to cool off in a former rock quarry that has become part of everyday life.

Towns With Personality to Spare

What connects these towns is not just history or attractions, but the way residents embrace their own stories. In La Grange, trains remain part of the daily soundtrack. In Bardstown, bourbon conversations tend to last longer than expected. Across Kentucky, these towns invite visitors into traditions that feel lived-in rather than staged. The result is a collection of places where quirks are not smoothed over, but shared openly, often with a smile.