10 Best Towns In Kentucky To Retire Comfortably

Are you approaching retirement? Searching for that perfect country lifestyle to enjoy your post-work life, or simply filling up the workday daydreaming about your ideal forever home? Plan your eternal sabbatical in Kentucky, home of breathtaking lakes and rivers, lush, green forests, and friendly small towns bursting with southern hospitality. Each of the following towns boasts low home prices and a slice of country living. Ride horses, fish, and paddle the clear blue waters, or become a bourbon connoisseur while you pick up the banjo or guitar. The possibilities are endless in the great state of Fun-tucky!

Bardstown

Bardstown is renowned as the Bourbon Capital of the World. They say it's like wine country, but with a southern accent. Located on Kentucky's Bourbon Trail, Bardstown boasts a rich history, as well as world-class drinks and dining, with eleven distilleries within 16 miles of the courthouse square, including the Bardstown Bourbon Company and Lux Row Distillers. Bardstown also offers numerous outdoor activities to stay active in your golden years. The nearby Bernheim Arboretum and Research Forest features over 40 miles of walking trails, preserved forests, and the famous forest giants, sculpted from reclaimed wood sourced directly from the forest itself.

There are also several golf courses in town, including the fabulous PGA Professional My Old Kentucky Home Golf Course, located next to the historic mansion, museum, and tourist attraction. With awe-inspiring natural views and affordable housing, Bardstown is a fantastic choice for your Kentucky retirement.

Hopkinsville

Just north of the Tennessee border, Hopkinsville is a beautiful city with small-town appeal and rural charm. With a main street lined with historic brick storefronts and outdoor recreation at your doorstep, Hopkinsville is the perfect town for an active yet peaceful post-working life. The 6th Street Historic District is home to tons of shopping and some great restaurants, like 6th Street Antiques and The Mixer, a restaurant, bakery and bar. Speaking of drinks, for a flight of world-class bourbon, the legendary Casey Jones Distillery is a quick drive to the edge of town.

Lying about 35 miles west of town is Land Between the Lakes National Recreation Area. Tucked between Lake Barkley and Kentucky Lakes, the park features 170,000 acres of forested land where you can boat, swim, fish, hunt, drive off-road vehicles, and camp. Numerous campgrounds and picnic areas offer access to the lake, as well as restrooms and scenic spots to dip your toes in the lake or spread out your picnic blanket and enjoy the views.

Elizabethtown

Less than a half-hour drive from Fort Knox, Elizabethtown is the perfect place to stock up all that gold you've been saving for your retirement. Unless, of course, you want to bet it all on a horse, in which case, the Kentucky Derby is only 45 minutes away (by car; it is substantially longer by horse).

Not that there is a shortage of things to do in Elizabethtown itself. The town features the Peddler's Mall, an antique and collectibles mall with over 200 vendors. Downtown is also dotted with restaurants and boutiques, and there are plenty of outdoor activities, including Freeman Lake Park, a 170-acre playground with kayak rentals and a boat launch, tennis and pickleball courts, and plenty of green space to roam.

Williamsburg

Enjoy nature and small-town life when you spend your retirement in Williamsburg. Not far from Cumberland Falls State Park in the Daniel Boone National Forest, Williamsburg certainly has its share of outdoor and aquatic activities, including along the Cumberland River. There are plenty of dining options in town, as well as the Williamsburg Vendors Mall, a large indoor flea market. Test your luck at the Mint Gaming Hall, with live sports betting, entertainment, signature cocktails, and great eats.

Though the town is small and rural, the Baptist Health Medical Group has a small medical center in Williamsburg and operates hospitals in nearby Corbin and Pinesville. With low housing prices and camping, boating, hiking, and swimming all in close proximity, Williamsburg is the perfect Kentucky town for your active outdoor retirement.

Covington

Situated directly across the Ohio River from Cincinnati, Covington has historic architecture, low home prices, a strong sense of community, and a superbly walkable riverfront, complete with shopping, dining, and arts and entertainment. Home to a staggering nine stops on the Kentucky Bourbon Trail, including the Wiseguy Lounge and the Revival Vintage Bottle Shop, Covington is a fantastic town for whiskey aficionados. The Behringer-Crawford Museum in Devou Park is a must-visit, with tons of unique and interactive exhibits, including the famous two-headed calf.

The small city's location on the Kentucky-Ohio border is ideal for travel. While Cincinnati is the closest major city, Covington is only about an hour from Louisville, as well as Ark Encounter, a full-scale model of the biblical Ark. With the Cincinnati skyline stretching out to the north and the bluegrass forests of Northern Kentucky just to the south, Covington provides the best of both city and country living!

Russellville

Quietly napping in southern central Kentucky, Russellville is a friendly small town with a vibrant community and more outdoor recreation than you can shake your hiking stick at. Baker Natural Area includes an easy loop and small pond, great for a stroll and some birdwatching, and Logan County Glade State Nature Preserve sits on 42 acres of protected limestone glades with a short but moderately challenging trail to get the heartrate going. For a completely different experience, explore the nation's only underground boat tour at the Lost River Cave, which also includes miles of hiking trails and a seasonal butterfly habitat.

With housing prices below the national and state averages, you can stretch your retirement budget while enjoying at Carrico Park Square, including a summer concert series that features a range of live performances and food trucks once a month from May through August. Russellville boasts small-town rural life balanced with access to world-class entertainment and culture.

Maysville

Spend your golden years on the banks of the mighty Ohio River, boating, fishing, or relaxing on the rivershore, filled with playgrounds for the grandkids and food and shopping for you to enjoy. Maysville hosts several annual festivals, such as Pig Out Maysville, with live music, art shows, and all the country fair fixings. What makes the community event even more special is that all of the proceeds go to the Shriners Transportation Fund.

Another great place for whiskey fans, Maysville is known as the birthplace of bourbon and home to the Old Pogue Distillery, a fantastic venue for learning about the history of the spirit. Explore some culture at the Washington Opera House, which dates back to 1898, and houses the famous Maysville Players, who perform musicals, comedies, and dramas, and visit the National Underground Railroad Museum to get a better sense of Kentucky's role in this essential piece of American history.

Madisonville

Madisonville just may be the best town to retire in all of bluegrass country, featuring tons of outdoor recreation and extraordinary dining options, from some of the state's best BBQ at Mallett Brothers and Larry's Country Style BBQ, to the infamous anaconda burrito at Acapulco Mexican Grill (bet you can't eat the whole thing!).

This small town goes big when it comes to throwing a party. The Hopkins County-Madisonville Fair is a week-long celebration that includes arena events, pageants, agricultural shows, rides, food, and fun for the whole family. Featuring disc golf, hiking, pickleball, as well as swimming, boating, and fishing at several lakes in the surrounding area, including Lake Peewee and nearby Lake Venus, Madisonville is a spectacular little town to call home.

Monticello

Have you considered spending your retirement on the lake? Literally, on the lake? Monticello, the county seat of Wayne County, is the home of Lake Cumberland and is known to be the houseboat capital of the world. Giving a whole new meaning to the term lake house, Monticello lies in the heart of the Cumberland Plateau and is a nature lover's fantasy come to life. History buffs can immerse themselves in the area's rich past at the Wayne County Historical Museum, which hides a system of limestone caverns in its basement. Take a gander at the historic overshot water wheel at the Mill Springs Mill and take the dog for a walk around the lake in the adjacent park.

Monticello features affordable housing and Wayne County Hospital's state-of-the-art medical facilities. With ample opportunity for hiking, off-roading, camping, fishing, boating, and swimming at Lake Cumberland State Park, you can spend your retirement in the great outdoors of western Kentucky, on or near one of the most popular lakefronts in the region.

Pikeville

Last but certainly not least on our tour of the finest retirement destinations in the Bluegrass State is Pikeville. This Appalachian gem, home of the storied Hatfield and McCoy family feud, has a rich arts community with the Appalachian Center for the Arts at the heart of the action, where local talent and visiting artists make their mark on East Kentucky.

You can also do some horseback riding on a three-mile trail overlooking Pikeville at H&M Stables, or enjoy fishing, kayaking, swimming, and hiking at Breaks Interstate Park, less than an hour's drive away. Thanks to its impressive terrain and breathtaking landscape, it has been dubbed The Grand Canyon of the South. Spend your golden years where nature and culture collide in the peace and serenity of the Appalachian Mountains!

Final Word

Spend your retirement fishing and boating, taking in live music and history, hiking, riding, and betting on horses. Complete with Southern hospitality and the best bourbon in the world, Kentucky is the ideal state for living your retirement dream. A mecca for lovers of nature, music, and a slower pace of life, the Bluegrass State is affordable, accessible, and filled to the bourbon-glass brim with culture and entertainment.