The 10 Best Places to Retire in Kentucky in 2021

Surround yourself with rolling hills and beautiful sunsets when you retire to Kentucky, the Bluegrass State. Kentucky is an affordable and beautiful state for retirees who want to enjoy a tranquil lifestyle and reconnect with nature. 

NewHomeSource is highlighting the top 10 cities for retirees in Kentucky. We want to make it easy for you to find the perfect community for your dream retirement in Kentucky — and find the perfect new retirement home! And don’t forget to cross-reference this list with our list of safest Kentucky cities to make sure you are moving to your ideal city.

Top 10 Cities to Retire in Kentucky

1. Middlesboro

Percentage of the Population Over 65: 17.4%

Median Home Value: $91,500

Most Recent Annual Number of Violent Crimes: 24

Most Recent Annual Number of Property Crimes: 366

Number of Hospitals Within 25 Miles of the City: 5

Found in the southeastern corner of Kentucky, Middlesboro is a gem that gleams with the potential for a comfortable and enriching retirement. Situated near the Cumberland Gap, this city is uniquely positioned at the junction where Kentucky, Tennessee, and Virginia meet. A short drive will take you to larger cities such as Knoxville, Tennessee, and Lexington, Kentucky, providing access to metropolitan amenities without the hustle and bustle.

Enjoy a scenic retirement when you make your home in the heart of the Cumberland Gap. Middlesboro, KY gives outdoorsy adults plenty of ways to stay healthy and enjoy Mother Nature. From hiking up to the Tri-State Peak to spending the day boating on the beautiful Fern Lake, you will always have something to do in Middlesboro.

Known affectionately as the “Gateway to the Cumberlands,” Middlesboro boasts a unique geological history. It is one of the few cities in the world built entirely within a meteorite impact crater. This intriguing aspect adds a layer of charm and curiosity, making it a topic of conversation and pride among locals.

Middlesboro offers a slower pace of life with the backdrop of the Appalachian Mountains. Cumberland Gap National Historical Park is a haven for nature enthusiasts, offering hiking, bird watching, and historical tours that tell the story of early pioneers. The Middlesboro Country Club, touted as one of the oldest continuously played golf courses in the United States, provides an excellent spot for golf aficionados to perfect their swing amidst scenic views.

Cultural and historical attractions abound in Middlesboro. The Bell County Historical Society and Museum offers a deep dive into the local heritage, while the Cumberland Gap Artist Co-op showcases works from regional artists, perfect for those who appreciate the arts.

Entertainment and dining in Middlesboro are delightful. Local eateries serve up hearty Southern cuisine, with an emphasis on comfort food that feels like home. The shopping experience is quaint yet satisfying, with locally-owned boutiques offering unique finds and personalized service. For entertainment, the area hosts various festivals and events throughout the year, such as the Levitt AMP Middlesboro Music Series, which brings live music to the heart of the town.

For those interested in staying active, Middlesboro has facilities for tennis and the increasingly popular sport of pickleball. The Middlesboro Tennis Center is a hub for local enthusiasts. Additionally, the town’s parks, such as the Middlesboro City Park, provide ample space for walking, picnicking, and enjoying the natural beauty of the area.

Grandchildren visiting Middlesboro will find plenty to keep them entertained. The town’s parks and recreational areas offer playgrounds and open spaces to explore. Seasonal events and community gatherings often feature family-friendly activities, ensuring that visits are memorable and engaging.

Healthcare in Middlesboro is well covered by Middlesboro ARH Hospital. The presence of this well-regarded healthcare facility offers peace of mind to retirees and their families. Senior centers, such as the Bell-Whitley Community Action Agency, provide resources and activities specifically geared toward older residents.

Middleboro is a beautiful site to spend your golden years. Get ready to fall in love with a Middleboro new home that will be the ideal launching point for all your retirement adventures.

2. Mayfield

Percentage of the Population Over 65: 16.3%

Median Home Value: $100,200

Most Recent Annual Number of Violent Crimes: 51

Most Recent Annual Number of Property Crimes: 467

Number of Hospitals Within 25 Miles of the City: 5

Nestled in the western part of Kentucky, Mayfield is a charming city with a unique blend of small-town hospitality and modern amenities. Located in Graves County, Mayfield is conveniently positioned near larger cities like Paducah, approximately 25 miles to the north, and Nashville, Tennessee, about two hours to the southeast. This proximity to major urban centers allows residents easy access to big-city conveniences.

Mayfield, often affectionately referred to as the “Queen City of the Jackson Purchase,” is known for its rich history and strong community spirit. One of its unique features is the preservation of its historical downtown, where charming boutiques, local eateries, and antique shops line the streets, providing a nostalgic ambiance reminiscent of a bygone era.

For retirees, Mayfield offers a plethora of attractions and activities. The Ice House Museum and the Wooldridge Monuments, often called “The Strange Procession That Never Moves,” offer intriguing glimpses into the area’s history and cultural heritage. Meanwhile, the Graves County Courthouse and the Confederate Memorial Gateway add historical depth to your explorations.

Take advantage of the parks and recreational facilities in and around Mayfield. Kess Creek Park is a local favorite with walking trails, a playground, and serene picnic spots. Enjoy outdoor adventures like hiking, fishing, and wildlife observation at the nearby Land Between the Lakes National Recreation Area.

Entertainment in Mayfield ranges from community theater productions at the Purchase Players Community Performing Arts Center to seasonal festivals that bring the community together in celebration. Varied dining includes a mix of local diners, Southern BBQ joints, and family-owned restaurants offering hearty, home-cooked meals. Shopping needs are met by a range of local shops and larger retail stores.

The Mayfield-Graves County Senior Citizens Center offers social activities, fitness classes, and educational programs designed to keep older adults engaged and active. Healthcare services in Mayfield are robust, with Jackson Purchase Medical Center providing comprehensive medical care, and nearby hospitals in Paducah offering specialized treatments.

Mayfield stands out as an ideal retirement destination due to its blend of historical charm, modern amenities, and strong sense of community. Mayfield offers a well-rounded and fulfilling retirement experience that rivals other locales.

3. Ashland

Percentage of the Population Over 65: 18.3%

Median Home Value: $102,800

Most Recent Annual Number of Violent Crimes: 73

Most Recent Annual Number of Property Crimes: 813

Number of Hospitals Within 25 Miles of the City: 6

Ashland, Kentucky, sits nestled in the heart of the Bluegrass State. It is a world away from the frenetic pace of Louisville or Lexington, those twin beacons of Kentucky culture. Here, time moves at a different rhythm, slower, steadier. Folks call it the “River City,” a nod to its position on the Ohio River, a watery thoroughfare that has been a lifeblood for generations.

Ashland is a place that whispers its charms. The cost of living is gentle on the wallet. This safe and affordable city has a fun culture. You will find plenty to occupy your days, from exploring the Booth National Historic Site, a window into the life of a legendary actor, to discovering hidden gems at the Ashland Art Center. Be sure to visit the historic Camayo Arcade and the Highlands Museum and Discovery Center.

The surrounding countryside is a canvas painted with rolling hills, sparkling lakes, and dense forests. For the outdoorsy type, hike, fish, and boat at Buckhorn Lake, or explore the rugged beauty of Carter Caves State Resort Park. Ashland’s Central Park has great walking trails for nature lovers. 

Evenings offer a mix of low-key entertainment. The Paramount Arts Center hosts a variety of shows, from live music to theater. For a more casual night out, there are cozy local pubs and restaurants serving up delicious cuisine.

While Ashland may not have the bustling energy of a big city, it compensates with a genuine warmth and a strong sense of community. Volunteer at the local senior center, join a book club, or simply making new friends. Start the next chapter of life in this welcoming Kentucky locale.

4. Shively

Percentage of the Population Over 65: 16.8%

Median Home Value: $107,000

Most Recent Annual Number of Violent Crimes: 54

Most Recent Annual Number of Property Crimes: 533

Number of Hospitals Within 25 Miles of the City: 14

Shively is a thriving Louisville suburb that is about a 15-minute drive from famous Churchill Downs. Most of the residents have Derby Fever year-round, not just on the first Saturday in May when thoroughbreds run for the roses. This great community allows you to sample Derby City’s funky culture and skip the constant noise and high price tags that come with living in an urban hub.

“The Gateway to the South End,” Shively, is nestled in the heart of Jefferson County. It is known historically for its bourbon production, with the historic Stitzel-Weller Distillery being a notable landmark. Retirees might find the city’s small size appealing, providing a sense of community and familiarity that’s often lost in larger cities.

For those considering a move to Shively, the city offers several attractions and amenities tailored to various interests. The Farnsley-Moremen Landing, a historic riverfront estate, provides a glimpse into the 19th-century life along the Ohio River, while the nearby Waverly Hills Sanatorium offers a more eerie but intriguing exploration of local history.

Shively Park is a local favorite where you can take a stroll, picnic, or enjoy a community event. Additionally, the Jefferson Memorial Forest, just a short drive away, provides expansive hiking trails, fishing spots, and serene picnic areas, making it perfect for a day out with visiting grandchildren.

Entertainment in Shively ranges from local festivals and community gatherings to nearby Louisville’s vibrant arts scene, including the Kentucky Center for the Performing Arts and the Louisville Orchestra. The dining scene in Shively and its vicinity is diverse with an array of delicious dining and bourbon.

Social clubs, hobby groups, and fitness classes specifically tailored for seniors will fill your calendar. The city boasts excellent healthcare facilities with several nearby hospitals, including Norton Hospital and Baptist Health Louisville. For those who love staying active, Shively offers several golf courses, tennis courts, and the increasingly popular pickleball courts.

Shively might just be the prime location for a vibrant retirement. The balance of tranquility and proximity to Louisville’s urban offerings ensures that retirees can enjoy the best of both worlds, making Shively the Kentucky city for you!

5. Covington

Percentage of the Population Over 65: 12.4%

Median Home Value: $111,500

Most Recent Annual Number of Violent Crimes: 188

Most Recent Annual Number of Property Crimes: 1,176

Number of Hospitals Within 25 Miles of the City: 25

Covington, KY lets seniors enjoy an exciting urban retirement, while still providing a peaceful and serene setting to call home. Covington’s great placement as a Cincinnati suburb gives active adults a private community, without sacrificing urban entertainment and amenities.

Covington, where the Midwest meets the South, is a place where the river bends and history settles like a fine wine. Nestled across the Ohio River from Cincinnati, they call it the “Gateway to the North.” It is a city in the throes of a renaissance. From grand Victorian mansions to trendy lofts, this area with its burgeoning arts scene is a win. Covington is known for its rich architectural heritage and stories of riverboat gamblers and industrial titans.

Imagine strolling through historic neighborhoods, popping into quaint boutiques, and indulging in world-class dining. The Behringer-Crawford Museum is a treasure trove of local history, while the Covington & Northern Kentucky Historical Society offers a deeper dive into the region’s past.

Covington is a gateway to the Ohio River, perfect for kayaking, fishing, or simply soaking up the sun. Devour Park, with its green spaces and playgrounds, is a lovely spot for relaxation or a picnic with the grandkids.  

Kenton County Senior Center offers a range of activities to keep you fit and engaged. St. Elizabeth Healthcare is a regional leader, providing a comprehensive range of services. Golf, tennis, and pickleball enthusiasts will find several options nearby, including public and private courses.  

It is easy to see why Covington has made the list with its excellent location close to Cincinnati. With a variety of attractions, amenities, and friendly atmosphere, it is affordable without sacrificing quality of life. Feel truly at home in your golden years in Covington.

6. Owensboro

Percentage of the Population Over 65: 17.5%

Median Home Value: $113,400

Most Recent Annual Number of Violent Crimes: 135

Most Recent Annual Number of Property Crimes: 2,432

Number of Hospitals Within 25 Miles of the City: 5

Retirees looking to invest in a fun urban retirement should consider living in Owensboro, KY. Nestled in the western part of the state, Owensboro is a city that promises more than just a comfortable living – it offers a lifestyle rich in culture, history, and a sense of community. Situated along the southern bank of the Ohio River, Owensboro is approximately 110 miles southwest of Louisville and 130 miles north of Nashville, Tennessee, providing easy access to big-city amenities.

This lovely city has many local parks, so you can stay healthy and enjoy nature. Owensboro also has a thriving culture of museums – like the Bluegrass Music Hall of Fame & Museum – so you can enjoy the great indoors, too! Known affectionately as the “BBQ Capital of the World,” Owensboro is renowned for its unique style of barbecue, particularly mutton, which draws visitors from far and wide, especially during the annual International Bar-B-Q Festival.

Looking for engaging activities and amenities? The revitalized downtown area features the scenic Smothers Park, often cited as one of the best riverfront parks in the country. It offers picturesque walking trails, a fantastic playground for visiting grandchildren, and a beautiful cascading waterfall. The park is a hub for numerous events and festivals.

Culture buffs will appreciate the Owensboro Museum of Fine Art, which hosts an impressive collection of regional and international art. The Western Kentucky Botanical Garden is another gem, providing a serene escape into nature with its meticulously maintained gardens and frequent educational programs. The Owensboro Museum of Science and History offers engaging exhibits and interactive displays that cater to all ages.

The healthcare infrastructure in Owensboro is anchored by Owensboro Health Regional Hospital, a comprehensive medical facility offering a wide range of specialties and services. Several senior centers, like the Elizabeth Munday Senior Center, provide a variety of programs tailored to older adults.

Golf enthusiasts can tee off at the picturesque Ben Hawes Golf Course or the more challenging Panther Creek Golf Club. Tennis and pickleball courts are scattered throughout the city, including at the inviting Moreland Park.

Get ready to enjoy life on your terms in Owensboro. Discover a retirement destination with small-town friendliness and big-city amenities. Thrive in your retirement. Whether you’re drawn by the allure of its famous barbecue, the charm of its riverfront, or the richness of its cultural scene, Owensboro, Kentucky, is a city that promises to make your golden years truly shine.

7. Hopkinsville

Percentage of the Population Over 65: 16.4%

Median Home Value: $116,000

Most Recent Annual Number of Violent Crimes: 90

Most Recent Annual Number of Property Crimes: 1,084

Number of Hospitals Within 25 Miles of the City: 7

When you make your home in Hopkinsville, you can stay active and enjoy a fun rural retirement. Hopkinsville, Kentucky, is a quiet oasis nestled in the heart of the Bluegrass State. It is a comfortable drive from larger cities like Nashville, Tennessee, and Louisville, Kentucky, offering the best of both worlds: small-town life with proximity to big-city amenities.

Nature lovers can go hiking in Jeffer’s Bend Recreation Area. The Casey Jones Distillery is a great way for active adults to take a walk on the wild side. Known affectionately as the “Batter Capital of the World,” Hopkinsville has a surprising industrial backbone. The city is a major producer of baking mixes, a fact that might surprise those who picture Kentucky solely as horse country.

Spend your mornings strolling through the serene Pennyroyal Park, afternoons exploring history at the Trail of Tears Commemorative Park, and evenings enjoying live music at one of the town’s cozy venues. The city’s museums, while modest in size, pack a punch. And for those who crave outdoor adventures, the nearby Land Between the Lakes National Recreation Area is a playground of hiking, boating, and wildlife spotting.

The city caters to its older residents with a variety of senior centers providing social activities, fitness programs, and health resources. Healthcare is reliable, with hospitals equipped to handle most medical needs. Golf and tennis enthusiasts will find options to suit their skill level.

Hopkinsville has a strong sense of community. If you are ready to leave the hustle and bustle behind, this locale will let you relax and enjoy life’s simple pleasures. Hopkinsville might just be your ticket to retirement bliss.

8. Somerset

Percentage of the Population Over 65: 19.1%

Median Home Value: $118,800

Most Recent Annual Number of Violent Crimes: 35

Most Recent Annual Number of Property Crimes: 258

Number of Hospitals Within 25 Miles of the City: 4

Near the shores of the Cumberland River is Somerset. This community in Pulaski County is strategically positioned in south-central Kentucky. This locale makes it easily accessible to larger cities like Lexington and Louisville, both within a two-hour drive. Known affectionately as the “Gateway to Lake Cumberland,” Somerset’s unique identity is closely tied to this stunning man-made reservoir, one of the largest in the United States.

The city’s proximity to Lake Cumberland not only provides breathtaking views but also offers a plethora of recreational activities that make Somerset an attractive destination for outdoor enthusiasts. Retirees will find solace in the area’s serene parks. General Burnside State Park is a lush river island that gives you plenty of opportunities to enjoy boating, swimming, and hiking. Pulaski County Park, with its scenic trails and fishing opportunities, provides a tranquil escape into nature.

Feeling adventurous? Learn more about things that go bump in the night at the International Paranormal Museum and Research Center. Somerset is renowned for its vibrant arts scene and rich cultural heritage. The Carnegie Community Arts Center, a historic building turned cultural hub, hosts a variety of events, from art exhibits to live performances. History buffs will appreciate the Mills Springs Battlefield Museum, which offers a fascinating glimpse into Civil War history. The Master Musicians Festival is a must-attend event, showcasing a diverse range of musical talents.

The Center for Rural Development regularly hosts concerts, theater productions, and community events. Lake Cumberland Speedway offers thrilling races for those who enjoy a bit of high-octane excitement. Easy dining and varied shopping add to Somerset’s appeal.

Retirees will find a supportive community with numerous activities geared towards older residents. The Somerset Senior Citizens Center offers a range of programs. Make memories with the grandkids at SomerSplash Waterpark.

Lake Cumberland Regional Hospital serves the area. Several clinics and specialized healthcare providers ensure that your healthcare needs are met with quality care. The availability of golf courses and, tennis courts translates to great activity and fun.

Somerset will be a great setting for your retirement in Kentucky. With all the amenities and services you crave, Somerset is a unique option for your golden years. Take a look at this inviting community.

9. Paducah

Percentage of the Population Over 65: 19.5%

Median Home Value: $118,400

Most Recent Annual Number of Violent Crimes: 71

Most Recent Annual Number of Property Crimes: 1,306

Number of Hospitals Within 25 Miles of the City: 6

Paducah is nestled along the Ohio River and Kentucky-Illinois border. Live close to the Missouri Boot Heel with Memphis and St. Louis within a comfortable drive. They call it the “Cradle of Aviation” here, a nickname earned when the Wright Brothers’ first airplane soared across the Kentucky skies. But that’s just one chapter in Paducah’s story.

The city is known for supporting both performing and visual arts, so those with a creative disposition will love retiring here. Called “Quilt City USA”, Paducah has a long history of quilting, and the Quilt Museum attracts visitors from across the globe. Here you can immerse yourself in exhibits and learn techniques from the experts. You will want to carve out time to attend a workshop or the annual quilting events.

This isn’t your average small-town life. Paducah is an artist’s colony, a riverboat gambler’s dream, and a nature lover’s paradise, all wrapped into one. The Lower Ohio River Museum and Steamboat Planetarium offer a glimpse into the town’s riverboat past, while the Carson Center hosts touring Broadway shows and concerts. If you’re more inclined to the outdoors, the Land Between the Lakes National Recreation Area is your oyster, offering everything from hiking and biking to fishing and camping.

For the golden years, Paducah offers a slower pace without sacrificing amenities. Golf courses dot the landscape, and the city has a burgeoning pickleball scene. The Paducah Senior Center is a hub for social activities, from card games to computer classes. And when it comes to healthcare, Lourdes and Baptist Health Paducah provide comprehensive services.

Dining is a treat. Paducah’s restaurants offer a mix of Southern comfort food, riverboat cuisine, and international flavors. Shopping is a delightful pastime, with unique boutiques and antique stores lining the streets. And for those precious visits from the grandkids, there’s always the local zoo, the Children’s Museum of Paducah, or a day out on the river.

Paducah is a place where the past and present intertwine, where art meets nature, and where a slower pace of life doesn’t mean a lower quality of living. It is a great place to enjoy Kentucky and all it has to offer!

10. Henderson

Percentage of the Population Over 65: 17.6%

Median Home Value: $120,700

Most Recent Annual Number of Violent Crimes: 81

Most Recent Annual Number of Property Crimes: 747

Number of Hospitals Within 25 Miles of the City: 8

Henderson is located along the Ohio River, near the intersection of the Kentucky-Indiana borders. Henderson offers a serene yet vibrant lifestyle that retirees will find both invigorating and comforting. The Henderson area is known for its duck and goose hunting.

Notable attractions here include John James Audubon State Park, home to the John James Audubon Museum. John James Audubon, the world famous wildlife artist, lived in Henderson and operated a business. You will also discover the OVAL Gallery and the annual barbecue and blues festival, W.C. Handy Blues & Barbecue Festival. Stroll along the historic downtown streets of Henderson and sit a spell at a café and enjoy a meal of freshly caught fish.

Enjoy small-town warmth and the convenience of nearby metropolitan areas. Evansville, Indiana, just across the river, provides access to a broader array of services and entertainment. Nashville, Tennessee, and Louisville, Kentucky, are both within a few hours’ drive, offering an easy escape for day trips or weekend getaways.

Discover interests that speak to you. The John James Audubon State Park includes a engaging museum, beautiful trails for hiking, and serene spots for bird watching—perfect for those who appreciate the great outdoors. Meanwhile, the city’s historic downtown district is dotted with quaint shops, inviting cafes, and charming boutiques, making for leisurely afternoons of exploration and indulgence.

The Henderson Fine Arts Center is a cultural beacon, offering a variety of performances, from theater to concerts, ensuring that the arts are never far from reach. For those who enjoy a more active lifestyle, the city provides ample opportunities to stay fit and engaged. Golf enthusiasts can tee off at the picturesque Henderson Country Club or the Municipal Golf Course, while tennis and pickleball courts are scattered throughout the city’s parks.

Serving retirees is the Henderson County Senior Services Center with a variety of programs. Healthcare needs are well catered to, with the Methodist Hospital offering comprehensive medical services and specialized care. For those needing more specialized treatment, the nearby Deaconess Hospital in Evansville is easily accessible.

When the grandchildren come to visit, Henderson shines even brighter. The city’s parks and recreational facilities are perfect for family fun, with playgrounds, swimming pools, and seasonal events. The Henderson County Public Library offers engaging programs for children, making it a great spot for a quiet, educational afternoon.

Henderson finishes out our list and shines with its embracing lifestyle. This is a city where the rhythm of the river and the melody of the blues provide a soundtrack to a life well-lived. Henderson, Kentucky, is an enticing choice.

NewHomeSource pulled data from the FBI Uniform Crime Reporting Services, Medicare’s Hospital Compare and the U.S. Census Bureau. In the event exact crime data was unavailable, estimates were used. Median home price, number of hospitals, 65+ population, and crime rates were entered into an algorithm to calculate a score for each city whose population is at least 10,000.

Common Questions About Retiring in Kentucky

City Name	People Over 65	Violent Crimes	Property Crimes	Access to Doctors	Median Home Price
Middlesboro	17.4%	24	366	4	$91,500
Mayfield	16.3%	51	467	4	$100,200
Ashland	18.3%	73	813	6	$102,800
Shively	16.8%	54	533	7	$107,000
Covington	12.4%	188	1,176	18	$111,500
Owensboro	17.5%	135	2,432	2	$113,400
Hopkinsville	16.4%	90	1,084	2	$116,600
Somerset	19.1%	35	258	2	$118,800
Paducah	19.5%	71	1,306	3	$118,400
Henderson	17.6%	81	747	4	$120,700
Glasgow	20.9%	26	433	2	$121,600
Bardstown	14.6%	15	348	4	$123,500
Madisonville	17.4%	30	294	2	$125,000
Winchester	16.7%	45	826	9	$128,200
Radcliff	13.0%	68	812	3	$129,100
Lawrenceburg	12.9%	4	123	7	$131,100
Frankfort	16.1%	96	1,013	6	$130,900
Erlanger	14.5%	16	156	15	$136,100
Berea	13.2%	26	229	2	$139,300
Newport	13.8%	37	547	18	$144,000

Access to Doctors is calculated by finding the number of hospitals, discounting children’s hospitals and VA hospitals within one mile of the city.