Downtown Historic District in Shelbyville, Kentucky. Image credit Blue Meta via Shutterstock

11 Best Small Towns In Kentucky For Retirees

Known as the Bluegrass State, because of the color appearance of grass when once seen from a distance in expansive pastures and fields, especially in the northern parts of the state, Kentucky boasts several features that will be of interest to retirees. For starters, Kentucky exempts all Social Security income from taxation. And while that’s a huge draw, it does not end there. For seniors earning other types of income, the birthplace of KFC provides significant deductions that can see one save loads of cash.

Featuring a landscape that varies from the mountainous terrains of eastern Kentucky — to the sumptuous rolling hills and vast plains on the western side, the world’s bourbon capital also plays host to a delicious array of charming small towns where the pace of life is slow, people are incredibly friendly, and opportunities for adventure are numerous. If this is what you are looking for, discover the 11 best small towns in Kentucky for retirees.


Lancaster United Methodist Church, located at 200 Stanford Street (U.S. Route 27/Kentucky Route 39) in Lancaster, Kentucky, United States
Lancaster United Methodist Church. Public domain, via Wikimedia Commons

Lancaster reclines at the intersection of Highways 27 and 52 at the foothills of the Appalachian mountains. Home to about 4,000 residents, Lancaster consists of small, tightly-knit communities that live in deliciously rustic settings — and in rural environments where life is simple, authentic, and quiet. Living here affords residents the opportunity to get acquainted with members of the Amish community and hence, witness first-hand a lifestyle that is reminiscent of an unsophisticated bygone era.

Herrington Lake, the state’s deepest lake, offers several outdoor opportunities for residents, including swimming and boating. Plus, boasting some of the finest fishing experiences in Kentucky, this gorgeous waterbody is also reputed to be among the state’s most beautiful lakes. Finally, since Lexington is just about an hour’s drive away from Lancaster, social amenities, including top-tier health facilities, are always within easy reach.


Pylons out front of the Graves County Courthouse in Mayfield, Kentucky.
The Graves County Courthouse in Mayfield, Kentucky. Image credit Roberto Galan via Shutterstock

Secreted in the southwestern corner of the state, Mayfield is an antiques paradise that is also often ranked among the best places to retire in Kentucky. Home to about 10,000 residents, a retiree in Mayfield will have a blast enjoying the town’s many attractions and pleasures. Shopping at Pear Tree Mall, for instance, will quickly become an addictive pastime — whether one is looking for interesting knick-knacks or big-item purchases.

Weekends can be spent on the nearby sparkling waters of Kentucky Lake, one of the country’s finest spots for crappie fishing. The largest lake east of the Mississippi also features two state parks: Kentucky Dam Village and Kenlake. If the number of its rustic cottages is anything to go by, the former arguably boasts more accommodation choices than any other Kentucky state park.


The City of Shelbyville’s redesign of Sixth Street is in the heart of the Historic Distric
Downtown Shelbyville, Kentucky. Image credit Blue Meta via Shutterstock

The Saddlebred Capital of the World — is how Shelbyville is known. And here is the truth. Few experiences can compare with the thrill and adventure of spending much of your golden years sitting on the densely muscled body of a horse, in this case, the American Saddlebred, and feeling its graceful power as it goes into a full gallop.

If you are sold on this, you will be tempted to make the Red Fern Riding Center, located about 11 miles away from downtown Shelbyville, your second home. Even if you have never ridden a horse before, this adrenaline-packed experience, which comes with great scenery and beautiful trails, will make you look younger with every ride. Plus, once in a while, you can enjoy the fun of picking apples, the fruit reputed to keep doctors away, at the often uncrowded Mulberry Orchard, a gorgeous family farm that boasts up to 16 varieties of apples.

Fort Thomas

Looking down the Historic Midway District of Fort Thomas, KY.
Historic Midway District of Fort Thomas, Kentucky. Image credit Wgpowers1998, CC BY-SA 4.0, via Wikimedia Commons

As a retiree with high-school-going children, you may be enthused by the fact Fort Thomas is home to Highlands High School. This 135-year-old institution is among the best-ranked high schools for football in the United States — and has been ranked by US News & World Report as the best in Kentucky for College Curriculum Breadth. But that said, retirement is often about your own experience. At Fort Thomas, you will keep your mind young and sharp at the Blue Marble Books, a wonderful little bookshop that features an incredible selection of reads for all ages. 

The City of Fort Thomas Museum, housed in a beautifully restored historic building, boasts an impressive collection of artifacts that bring Fort Thomas' past to life. Plus, Fort Thomas is a suburb of Cincinnati, Ohio, and hence, big-city amenities are close at hand. Fort Thomas also sits on the Ohio River and provides access to Coney Island Park.


A Coal Barge On The Ohio River At Bellevue And Dayton Kentucky Across From Cincinnati Ohio
Bellevue, Kentucky across from Cincinnati, Ohio.

Bellevue is a Kentucky treasure that plays host to about 5,500 residents and is a refreshing Neverland that checks nearly all retirement-relevant boxes. For a name that is translated as "Beautiful View" in French, a median home value (2021) of $148,900 sounds like a great bargain. This is all the more tempting, considering the country’s average was about $244,900 in 2021.

Bellevue is also a convenient 10-minute ride to downtown Cincinnati. This means if you accidentally twist your ankle while hiking at Bellevue Beach Park, a beautiful green-space gem that features heart-melting waterfront views, you can access Christ Hospital in Cincinnati, ranked an impressive 43rd in the country in orthopedics.


Old beautiful architecture building in Bardstown one of most beautiful town in Kentucky.
Old, beautiful architecture building in Bardstown, Kentucky. Image credit Jantira Namwong via Shutterstock

Welcome to the "Bourbon Capital of the World." Spending one’s sunset years in such a place involves enjoying the tongue-tingling caramel and vanilla flavors of a drink that Kentucky is best known for. Seniors often enjoy participating in the Kentucky Bourbon Festival, a September event that features boatloads of food trucks, samples of amazing bourbons, and fantastic music.

Besides, this Kentucky charmer is the official trailhead of the Kentucky Bourbon Trail — and will see one sipping premium spirits while inhaling some of the most heart-melting sceneries around. About three in 10 of Bardstown’s residents are aged 55 years and older. The implication is that retirees will be in good company reminiscing about the good old days — and plotting meet-ups and adventures every other weekend.


Treble Cycle sculpture by Mike Welch outside the federal building, Danville, Kentucky.
Treble Cycle sculpture by Mike Welch outside the federal building, Danville, Kentucky. Image credit View_Point via Shutterstock

Danville is in central Kentucky’s Bluegrass region and hosts about 17,300 residents. Known as the City of Firsts, Danville was Kentucky’s first capital. It hosts the state’s first courthouse and was the site for the writing and signing of the first constitution in Kentucky. Seniors will have many sites of historical interest to explore in and around the town, including the charming log house jail, the first post office west of the Allegheny Mountains, and the meetinghouse where Kentucky's first constitution was signed.

Besides retracing the footprints of the region’s pioneers, seniors can catch a movie at the Pioneer Playhouse, Kentucky’s oldest outdoor theatre. Just as interesting will be weekends spent at the Perryville Battlefield State Historic Site, one of the most intact battlefields of the Civil War.

Pewee Valley

The Wooldridge-Rose House, Kentucky.
The Wooldridge-Rose House, Kentucky. Image credit TEDD LiGGETT, CC BY-SA 4.0, via Wikimedia Commons

If you want to retire in a small town where residents are warm and friendly to the extent that neighbors know and help each other, Pewee Valley might be your best pick. This quaint, peaceful community is a Suburb of Louisville and hence, provides access to all the big-city services and pleasures that would be of urgent interest to a senior. Besides, Pewee Valley’s incidence of violent and property crime per 1,000 residents is 0 and 1.3, respectively — against national averages of 1.6 and 23.3, respectively.

At the Kentucky Artisan Distillery, you can learn what it takes to produce a fine-tasting bourbon, in settings that are heart-warming and lovely. Plus, if you love the tranquility of nature, you will be tempted to spend every waking moment at the Yew Dell Botanical Gardens, a stunning property that features a castle-esque building and unforgettable florals.


An aerial view of the countryside around Berea, Kentucky.
Countryside around Berea, Kentucky.

Berea is a Kentucky art paradise that boasts a population of about 16,500. The scenic town sits near the Cumberland Mountains, about 14 miles south of Richmond. Since it hosts the tuition-free Berea College, the first interracial and coeducational college in the South, this town is ideal for seniors wishing to remain young at heart. About 17% of Berea residents are aged 65 years and above, and for this reason, the town offers opportunities for seniors to meet and socialize with a like-minded crowd.

Seniors who pride themselves on being life-long learners will have several opportunities to pick up new skills, including jewelry-making, blacksmithing, and fiber arts. Art enthusiasts can make visiting Artisan Village a once-a-week routine — while the Berea Pinnacles hiking trails — often mentioned among the state’s best hikes, are ideal for seniors keen on keeping fit.


Historic commercial buildings in downtown Winchester, Kentucky.
Historic commercial buildings in downtown Winchester, Kentucky. Image credit Christopher L. Riley, CC BY-SA 4.0, via Wikimedia Commons

The Birthplace of Beer Cheese boasts a heart-ravishing Historic Downtown District that looks almost the same way it did more than 100 years ago — and which has been on the National Register of Historic Places since 1981. A senior looking for places to stretch while sampling quaint shops and eateries will want to visit the town’s downtown area as often as possible. Winchester is also small as it boasts a population of just about 18,900 — yet almost always vivacious — so that there is rarely a dull moment.

For seniors who put a premium on access to big-city services and amenities, this Kentucky gem is just about 34 minutes from Lexington, Kentucky’s second-largest city. Clark County Parks & Recreation is ideal for keeping the muscles firmed up and well-toned; the traffic in town is almost always light, and people know each other fairly well. Finally, seniors, those 65 years and above, make up over 16% of the town’s population — meaning the social circle will comprise folk with similar experiences.


Downtown street in Harrodsburg, Kentucky.
Downtown Harrodsburg, Kentucky.

For seniors looking to settle in places filled with history and charm, Harrodsburg is among Kentucky’s best choices. Founded in 1774, a good two years before the signing of the Declaration of Independence, Harrodsburg is reputed to be the oldest settlement west of the Alleghanies. Old Fort Harrod State Park is particularly a gem. Among its draws is the oldest cemetery west of the Alleghenies — as well as Lincoln Marriage Temple — a brick pavilion featuring the wooden cabin in which the parents of President Lincoln were once wed.

About 7 miles from downtown Harrodsburg, at the Shaker Village of Pleasant Hill, BBC News’ top hidden travel destination, stands what was once the third largest Shaker community in the United States, now beautifully restored and repurposed.

Known as the Bluegrass State, Kentucky offers seniors several options ideal for retirement. While the Bourbon Capital of the World does not boast a landscape that is as dramatic as that of California or Colorado, its topography features pieces and patches that are just as sweet and heart-melting. Nestled close to these sites are towns that are small, charming, and closely knit and, hence, the kind that will tickle the fancy of a senior looking forward to his retirement. Among this number are cute little gems such as Bardstown, Berea, Fort Thomas — and Mayfield.

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