9 Prettiest Main Streetscapes In Kentucky

The best main streets in Kentucky are those that tell a story. Paducah's Broadway Street tells the tale of the creativity of the artists and quilters who live there through a quilting museum and wall-to-wall murals on a river walk. Elizabethtown's Main Street still bears the scars of the Civil War, along with in-depth historical records of how settlers lived and worked preserved within a mansion. In Corbin, the downtown narrates the story of KFC from its humble beginnings as a cafe to a massive franchise. These are just a few examples of the many stories one can find by visiting these Kentucky towns, including sites related to famed and quirky Kentuckians like the creator of bourbon whiskey and the explorer Daniel Boone. You can see these stories firsthand at these 9 prettiest main streetscapes in Kentucky.

Paducah

Paducah's Broadway Street and indeed its entire downtown area are defined by creativity. That's why Paducah is a certified UNESCO Creative City, as it maintains a close connection to the arts. Not far from Broadway Street is the town's crown jewel: The National Quilting Center. The center displays the works of master quilters, both past and modern, along with classes teaching this art to newcomers. At the end of Jefferson Street, one can find the Paducah Wall to Wall Portraits of our Past, cataloging the area's history in expertly painted murals. In addition to art, the American Civil War left a deep impact on the town's culture. You can learn about this at the Lloyd Tilghman House & Civil War Museum, the home of a former Confederate General, or visit the Confederate Monument in Paducah, within the Maplelawn Park Cemetery & Mausoleum.

Frankfort

Frankfort is the capital of Kentucky, but it still hasn't let go of its small-town vibe, with just under 30,000 residents and several pioneer attractions dotting both its main street and the surrounding downtown area. Off of its Main Street is the grave of none other than Daniel Boone, the explorer who traversed the wild Bluegrass state, leaving behind many trails and forts along the way. Once you get on Main Street, you can see several unusual exhibits at the Capital City Museum, such as the origin of Bibb lettuce or the tooth of a giant mammoth found in Frankfort. You can tour the Greek Revival-style Kentucky Old State Capitol Building or see one of the oldest buildings in Kentucky at the 1796 Liberty Hall Historic Site. This museum was the home of the first Kentucky Senator, John Brown, and features exhibits on Native Americans, slavery, and Brown himself. Be careful, as the museum is rumored to be haunted by a ghost known as the Grey Lady on the second floor.

Elizabethtown

This town knows how to have fun. That's why locals call it Etown. Main Street Etown is both a bustling commercial district and a quirky historic spot. For example, on Main Street, there's an old Cannonball lodged into a building. That cannonball came from a Confederate artillery barrage upon the town, and it was left there by townsfolk. There's also the Brown-Pusey House, a 1825 Georgian Mansion that served as a board for General George Armstrong Custer in his attempt to deal with the KKK and illegal distillers in Etown. Today, the mansion is a museum, event center, and library with more than 2,000 volumes on early Kentucky pioneers and settlers. Main Street has several boutiques, like the O'Neal's Boutique at Back Home for women's apparel and Raiment + Boon, for the discerning customer.

Georgetown

Georgetown is one of the premier towns in Kentucky. With the Toyota plant providing significant job opportunities, Georgetown has become the fastest-growing city in the state, and that growth has come to its Main Street as well. A quick stroll down Main Street will take you to the Galleries at Georgetown College or Royal Spring Park, which is said to be the origin of bourbon. At this spot, Reverend Elijah Craig allegedly created bourbon whiskey, which would go on to become a classic Bluegrass beverage. At the end of Main Street is Ward Hall, a beautiful Greek Revival mansion built in 1957 for $50,000 in gold. One of its residents was the socialite Sallie Ward, who scandalized guests with her behavior, such as showing up naked to the party and even drawing the attention of Queen Victoria.

La Grange

La Grange is a friendly neighbor next to Louisville with an even friendlier downtown. The railroad was one of its key industries, and it keeps the railway spirit alive with its Main Street Train. This freight train takes passengers up and down its Main Street up to 30 times a day, making it a favorite mode of transportation for anyone wanting to explore it. One of the primary attractions on Main Street is the La Grange Railroad Museum & Learning Center, which collects freight cars and locomotives from the Louisville and Nashville Railroad, and has several dinner train events held throughout the year. There are several other fun spots off of Main Street, ranging from the Copper Awning Flea Market to Springs Park and the Oldham County History Center to check out.

Corbin

Main Street Corbin is the place to be if you're a big fan of Kentucky Fried Chicken. In this town, Colonel Sanders tried his hand at selling his secret recipe fried chicken to the public at a cafe. The recipe was a big hit and he went on to sell the cafe and start the KFC franchise. Today, his cafe is part of the Harland Sanders Cafe and Museum. Down south from the cafe is the Historic Engineer Street Bridge, which was originally used by the railway in 1902 but today is a walking bridge. On Main Street, there are several eateries, from the American Depot on Main to the fine dining steakhouse, The Fleur De Lis. As you travel through the Corbin area, you'll want to explore Cumberland Falls State Resort Park, home to a waterfall called the Niagara of the South.

Bardstown

Bardstown is widely regarded as the best town for a 3-day weekend getaway in Kentucky due to its bourbon distilleries, Civil War museums, and beautiful architecture. As you drive into town, you'll pass by the My Old Kentucky Home State Park, which contains the two-story Federal style mansion, Federal Hill, built in 1818. The poet Stephen Foster was inspired by this building to write Kentucky's state anthem: My Old Kentucky Home. Once you make it to the town's main road, called 3rd Street, you'll encounter several historic places such as The Old Talbott Tavern, built in 1779, making it the oldest building in Kentucky. Just off the main road is Old Bardstown Village & Civil War Museum and the Women's Civil War Museum, containing some of the largest collections of Western front artifacts from the Civil War. Right on Main Street, you can book a lovely dinner train ride via the My Old Kentucky Dinner Train.

Winchester

Winchester's Main Street is noteworthy for keeping the same look it has had for the past century. In its historic district, there are five globe lampposts, which give off the vibe of an old Victorian community. Don't let this old vibe fool you, as Winchester is an innovative town. This town was the birthplace of both beer cheese and the Ale-8 ginger ale. You can sample beer cheese by taking the Beer Cheese Trail, which will take you to Lomas' at the Opera House, right on Main Street. After trying out this dip, you can catch a show at the Leeds Center for the Arts, or learn about the entirety of Kentucky's history at the Bluegrass Heritage Museum. Just outside of downtown Winchester, you can dive into history at the Civil War Fort at Boonesboro or go a bit further into Fort Boonesborough State Park, a recreation of a fort established by Daniel Boone in 1775.

Glasgow

Glasgow is named after the city in Scotland and the homeland of one of the county commissioners who selected Glasgow as the county seat of Barren County. It maintained that Scottish spirit through the Glasgow Highland Games, which were replaced in 2023 with the Glasgow Gaelic Gathering, with workshops and classes on Scottish language, culture, and crafts held right off Main Street. In Main Street, Glasgow, and the surrounding area, there are several historic places to visit. First off, there's the 1934 Plaza Theatre, which puts on musicals and stage plays, including adaptations of Jane Austen stories. Further down the road off Main Street is Fort Williams, a makeshift military installation used during the American Civil War to defend Glasgow against Confederate General John Morgan's raids. Glasgow is also close to Cave City, an ideal spot for exploring Mammoth Cave National Park, the world's longest cave system.

Defined By Creativity

These main streetscapes are in many ways defined by their creativity, both of past figures and modern ones. You can view the creative charm of folks like Sallie Ward in Georgetown, or Colonel Sanders in Corbin, or the creator of bourbon in Georgetown. You can also see modern creativity all throughout towns like Paducah, with its expert quilters and river murals. While most of these streetscapes are highly walkable, you can also kick your feet up and relax with a Main Street Train ride in La Grange. No matter what you choose to do when you get there, these main streetscapes will delight you.