An aerial view panorama of the Kentucky river with a boat on the water. Image credit Cade Nathaniel Nicholson via Shutterstock.

7 Best Small Towns in Kentucky For A Weekend Escape

When imagining the US state of Kentucky might conjure up images of bourbon whiskey, the Kentucky Derby, and fried chicken. While those things are indeed commonplace in the Bluegrass state, there is more to Kentucky than meets the eye.

Kentucky has a great deal to offer if interested in Civil War history, art, and culture. Perfect for a road trip or weekend getaway, the state of Kentucky comprises 549 cities. Surprisingly, only two of them are home to over 100,000 inhabitants. If seeking small, rural towns to vacation in, read below about the seven best small towns in Kentucky for a weekend escape.


Bourbon capital of the world sign and downtown in Bardstown Kentucky.
Bourbon Capital of the World pavement sign. Image credit University of College via Shutterstock. 

Located in the heart of Kentucky's Bluegrass State in north-central Nelson County is Bardstown. Settled in 1780, it is Kentucky's second-oldest city. Home to eleven whiskey distilleries, it is trademarked as the "Bourbon Capital of the World" and makes it the ideal setting for the annual Kentucky Bourbon Festival.

Bardstown has a picturesque downtown, lending it the title The Most Beautiful Small Town in America by USA Today. The historic downtown is home to 200 buildings listed on the National Register of Historic Places, including the Old Talbott Tavern. An early stagecoach stop built in 1779, today it serves as  a bed & breakfast, tavern, and restaurant. My Old Kentucky Home State Park is right inside town. Its centerpiece is an old plantation home built in 1818 and open for tours.


A view of the abandoned, historic Waveland residence in Danville, Kentucky.
Abandoned Waveland Residence in Danville, Kentucky. Image credit The American Explorer via Shutterstock. 

In central Kentucky's Bluegrass region of Boyle County is Danville. Founded in 1792, it holds the title "The City of Firsts." Danville's firsts include the first Kentucky courthouse and the site of the Kentucky Constitution signing. Danville was the first capital of Kentucky, home to the first post office west of the Allegheny Mountains. Finally, the Kentucky School for the Deaf (KSD) is the first state-supported school in the US for deaf children.

Perryville Battlefield Park was a significant battlefield of the Civil War. Known as the most destructive civil war battle in Kentucky, more than 7,600 were proclaimed dead or missing. The Perryville Battle Reenactment is an authentic performance of this deadly scene.

The town contains many notable buildings, landmarks, and exciting museums. Warrenwood Manor is a historic property built in the Gothic Revival style. Today, it is a popular wedding venue. The Great American Dollhouse museum exhibits over 200 handcrafted dollhouses with meticulous detail. Twelve miles north of town is Herrington Lake. This 3,600-acre, manmade lake is ideal for fishing, camping, or relaxing in nature.


Aerial view of autumn at Barren River Lake in Kentucky
Aerial view of autumn at Barren River Lake in Kentucky. Image credit TravelEatShoot via Shutterstock. 

Glasgow is in central Barren County. Founded in 1799 by a group of Revolutionary War veterans from Scotland, the town shares the name of Glasgow, Scotland. The town received city rights in 1809, and its many historic homes still stand proud today. The city’s South Green Street has many homes in Colonial, Federal, and Victorian styles.

An important link in the Underground Railroad several Glasgow homes hid African Americans as they escaped from slavery. Notable is the Old Glasgow Seminary Home, under which were tunnels to hide escapees. The city is also home to Fort Williams, a restored Civil War-era battlefield with a cemetery. The fort protected the area from Confederate infantry raiders. About 15 miles southwest is the Barren River Lake State Resort Park. The park is the place to go for on-water recreation and features an 18-hole golf course, and short hiking trails.

The park hosts the city’s annual Scottish Highland Games. The multi-day event involves Scottish dancing, bagpipe performances, and athletic competitions such as tossing a heavy wooden pole, known as a caber. Adjacent to Barren River Lake is Brigadoon State Nature Preserve, with 187 acres of protected land, mature woodlands, impressive spring flowers, and resident and migratory birds.


White fence on horse pasture, Shaker Village of Pleasant Hill, Harrodsburg, Kentucky
Scenic views in Harrodsburg. Image credit Danita Delimont via Shutterstock.

Harrodsburg is in the heart of Kentucky's famed Bluegrass region, part of Mercer County. Founded in 1774, it is the oldest town in Kentucky west of the Allegheny Mountains. Named one of "Five hidden US Travel Destinations" by BBC NEWS magazine, Harrodsburg has a thriving pioneer heritage. Honored as the oldest permanent American settlement west of the Appalachians, Harrodsburg has many well-preserved buildings and destination landmarks.

Shaker Village of Pleasant Hill is 3,000 acres of historic property, prairie farmland, preserved buildings, and trail systems. The Kentucky Shakers were an early religious sect that inhabited the area and died out because of their celibate lifestyle. The town's Old Fort Harrod State Park has much to offer: a reconstructed fort; a museum; a federal monument; the oldest cemetery west of the Alleghenies; and finally, the Lincoln Marriage Temple – in which Abraham Lincoln's parents married.

Downtown Harrodsburg boasts many locally-owned restaurants and craft and antique shops. Visitors can catch a live theater show at downtown Ragged Edge Community Theater. A 10-mile drive east is the Chaplin River, visitors can rent canoes and kayaks to enjoy the water. Herrington Lake, approximately 10 miles west, features five marinas with boat rentals, varied lakeside dining options, and accommodations.


Victorian building in Maysville, Kentucky.
Historic buildings in Maysville, Kentucky. 

Maysville is located in Mason County, Kentucky, and on the edge of the outer Bluegrass Region.

Birthplace to bourbon whiskey, the city's access to the Ohio River made it ideal for exporting bourbon whiskey, hemp, and tobacco. Visitors can enjoy tastings and learn about bourbon at the Old Pogue Distillery, dating back to the Civil War. Incorporated in 1787, the city has significant ties to the Civil War. Maysville was also a stop on the Underground Railroad. The National Underground Railroad Museum operates inside the former home of the Bierbower family. The family housed enslaved people on the run. Visitors can see photos and items related to the railroad's history in the museum. 

Maysville’s historic downtown is home to two historic theaters. The Washington Opera Theatre is the fifth oldest theater in the US that is still operational. The Russell Theater premiered "The Stars are Singing." It is an elaborately decorated theater currently under construction to reopen. Outdoor lovers can enjoy boating and camping along the Ohio River in the city's Maysville River Park. At the same time, golf aficionados can enjoy four nearby courses.


Main street of Midway - a small town in Central Kentucky famous of its boutique shops and restaurants
Railroad track and boutiques in Midway. Image credit Alexey Stiop via Shutterstock.

Quaint Midway is in the northern section of Woodford County in Kentucky's Bluegrass region. It is the first town in Kentucky founded by a railroad. Named Midway because of its equal distance between Frankfort and Lexington, the city was initially just a railroad. Later on, the town built up around it. Today, train tracks bisect the city's business district, giving it a dash of nostalgia. Midway is the epicenter of the Thoroughbred horse breeding industry. Many of its prestigious breeding farms offer tours, including Three Chimneys, Pin Oak Stud, Margaux Farm, Lane's End Farm, and Airdrie Stud.

In 1978, 176 buildings in Midway were placed on the National Register of Historic Places. The register designates most of the town as significant to American history, architecture, art, archeology, engineering, and culture. Efforts to begin rejuvenating the city's downtown began in 2003. Today, visitors may enjoy a lively downtown with various dining options and storefronts. Midway visitors can take the short 10-mile drive southeast to Masterson Station Park. The park features horseback riding lessons, hiking trails, a playground, and a kid's splash pad.


Discovery Sculpture located at the National Quilt Museum in Paaducah, Kentucky
Sculpture at National Quilt Museum. Image credit David Hedrich via Shutterstock.

At the heart of America's inland waterways, in McCracken County, is Paducah. A sophisticated rivertown, it sits at the confluence of the Tennessee and the Ohio rivers.

Founded in 1827 by William Clark of Lewis & Clark fame, the city is a mix of culture, history, and art. Best known as "Quilt City," Paducah is a designated UNESCO creative city famous for fiber arts. The annual AQS QuiltWeek is a quilting contest where visitors can buy quilts and learn to quilt with world-class instructors. Also in town is the National Quilt Museum. The museum features a collection of contemporary quilts, expositions, and workshops.

The Paducah Wall to Wall Murals were initiated by Louisiana mural artist Robert Dafford. The murals decorate the city's flood walls, used to provide a level of protection against flooding from the Ohio river. These art installations and murals exist along the water as well as throughout the town, depicting Paducah's rich history. The city's downtown is a designated historic district listed on the National Register of Historic Places. It is a historic waterfront that features lively streets lined with designated historical buildings. Visitors can enjoy the town's Bob Noble Park, located right inside town. This 135-acre park is wheelchair accessible and features a lake with fishing piers, a swimming pool, play areas and sports facilities.


Clearly, Kentucky is much more than just Kentucky Fried Chicken, bourbon spirits, and horse racing. As seen from its many small, historical towns, Kentucky played a significant role in the Civil War, including hiding enslaved African Americans, as well as in fighting for freedom for all Americans. The state of Kentucky is proactive in protecting its many historic cities, landmarks, and cultural traditions. A state full of art and expression, Kentucky has something for everyone!

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