
Though the Bluegrass state is a fairly tax-friendly and economical place for retirees to settle down, those considering retiring to Kentucky are often drawn to this state because of its beautiful greenery, welcoming atmosphere, and milder climate. There are plenty of attractive places to retire in Kentucky too.
Kentucky is a mix of larger cities like Lexington and Louisville and farm country. Kentucky is the largest producer of beef east of the Mississippi and a significant contributor of wheat, corn, soybeans, and hay.
For seniors who love horses, Kentucky likely tops your list, being that it is at the heart of horse country. And retirees who love to ride will be most drawn to the Lexington area, the horse capital of the world. Of course, no one can forget that Kentucky is home to one of the country’s largest sporting events, the Kentucky Derby.
The Derby first started in 1875 and is hosted in Louisville, most often on the first Saturday in May. Attendees of this major event come from all over the world, and if you miss the race, you can always check out the Kentucky Derby Museum.
But you don’t need to love horses to enjoy Kentucky. Outdoor enthusiasts will appreciate the numerous adventures in Kentucky, such as spelunking in the many caves or rock climbing in the Red River Gorge. Plus, the Appalachians are found on the east side of Kentucky and are the ideal place for hiking, biking, horseback riding, fishing, ATVing, and camping.
Kentucky’s climate is best described as sub-tropical with warmer humid summers and cold but not frigid in the winters. The state does see some snow, but it isn’t even half of the national average. Kentucky is relatively unique in that it offers a variety of climates throughout the state, depending on if you choose the colder mountain regions or warmer southern towns.
The cost of living is slightly lower here than the national average. Plus, Social Security is not taxed, nor is any other retirement income up to $31,110. After the initial exemption, retirement does carry a tax of 5%. In addition to the friendly retirement income taxes, Kentucky’s property taxes are also lower than the national average, usually falling under 1%. Plus, there is a homestead exemption for seniors 65+.
However, Kentucky does have some less than ideal taxes that impact seniors, such as their capital gains tax and inheritance tax. The capital gains tax only impacts those of a specific income bracket, and the inheritance tax applies to non-direct relatives.

Where to Retire in Kentucky
- Louisville
- Bowling Green
- Frankfort
- Berea
- Pikeville
Louisville

- Percent of Senior Population: 14.9%
- Overall Population: 617,638
Louisville, located on the Ohio River in North Central Kentucky, is the largest city in the state. It is best known for being the home to the Kentucky Derby, but Louisville has a lot more to offer than just the Churchill Downs. The city’s people are a balanced blend of the south and midwest cultures, creating a friendly and welcoming community to newcomers. And much like its culture, the city’s architecture is a hybrid of historical and modern buildings and homes interspersed throughout Louisville.
Many retirees enjoy Louisville for its pedestrian-friendly atmosphere, allowing residents to easily access daily amenities on foot. Plus, active retirees looking to stay healthy will love the 12 parks, including Waterfront Park, Joe Creason Park, and Big Rock. And when you want to get out for more adventurous hikes, there are numerous places within an hour’s drive. Some of the best hiking outside of the city include Tioga Falls Trail, Jefferson Memorial Forest, and Charlestown State Park, all within a 40-minute drive from downtown.

Louisville has a vibrant art and theater culture and hosts the Humana Festival of New American Plays, which runs for six weeks. The Humana Festival has put on more than 450 different plays since it opened in 1976. In addition to the Humana Festival, Louisville also features the Kentucky Shakespeare Festival, Museum Ros, and several art galleries.
There are 16 distilleries in the city, making it an excellent place to take a bourbon distillery tour. But if whiskey isn’t your thing, there are a couple of wineries in town too. And of course, like any large city, there are several artisan breweries in Louisville too.
Unfortunately, the big drawback to this affordable city is that the crime rate here is higher than the national average.
Bowling Green

- Percent of Senior Population: 11%
- Overall Population: 70,543
Bowling Green, located in Kentucky’s southern region, is just an hour’s drive from Nashville. It is the third-largest city in the state. However, it is far from a major metropolitan, which is likely why they’ve so successfully maintained their southern hospitality yet still considered a forward-thinking city.
Bowling Green is very retiree-friendly with its milder climate and quick access to the city’s conveniences. Depending on where you live, most residents can easily get around on foot if they choose. And Bowling Green is the shopping, dining, and entertainment center for the ten nearby counties. The city ranks in the top for the most restaurants per capita in the country. The dining ranges from fast food to privately owned upscale dining, with a variety of global food options.

In addition to the shopping and dining in the area, Bowling Green has more than its fair share of museums, such as the Historic Rail Park & Train Museum, the Corvette Museum, Downing Museum, and the Riverview Historic House Museum. Plus, there are other cultural opportunities to check out, like the symphony, South Kentucky Performing Arts Center, and the Capitol Art Center.
For retirees looking to get outdoors and enjoy nature, Bowling Green has many caves to explore, which is why it’s referred to as cave country. The Lost River Cave is one of the most popular sites with its underground boat tours, miles of trails, wetlands, and a nature center. In addition to the caves, there are several parks and the Greenway trail for walkers, joggers, and cyclists. And if you enjoy spending time boating, kayaking, or fishing, you can always head over to the River Start Park or one of the two larger lakes Basil Griffin and Shanty Hollow, to spend time on the water.
Bowling Green may not be the city’s largest town, but they are home to the most frisbee golf courses in the area, not to mention seven traditional golf courses, both public and private.
In the summertime, Bowling Green hosts a free outdoor concert series, BB&T Concerts In The Park, from June to September. BB&T is located in the district in the downtown area.
Though the crime rate is higher than the national average the city seldom sees acts of violent crime.
Frankfort

- Percent of Senior Population: 16.1%
- Overall Population: 27,755
Frankfort is found in central Kentucky and is a small town full of activity and charm. One of the reasons this small town has more going on than other cities of its size is because it is the state capital, which adds to the community’s hustle and bustle.
Many historical buffs will find the town’s colorful history fascinating. Frankfort’s history includes being the resting place for Daniel and Ruth Boone, a Civil War site in which both sides occupied it, and boasts the Bourbon Ball’s birthplace created by two bold entrepreneurial women, Rebecca Goach and Rebecca Booe, in 1919.
One of the city’s most distinct characteristics is the Kentucky River that runs through the middle of town. The river plays an active role in day-to-day life for those who live in the area. It has a paved riverwalk for active retirees, parks, and an amphitheater that hosts various events throughout the warmer months. Plus, there is a public marina and free boat tours. And the river is perfect for those looking to go fishing, canoeing, and boating.

Retirees interested in a town with strong ties will find Frankfort’s many volunteer opportunities and clubs appealing. Two of the most active groups in the town include the Commonwealth Gardens, which promotes gardening throughout the town in parks and school grounds. The other club is WalkBike Frankfort, a group of active residents who make Frankfort a pedestrian and bicycle-friendly city.
The WalkBike group has successfully helped create interconnecting paths throughout the town, giving residents easier access to the local amenities. And it’s not just the residents of Frankfort that take advantage of the paths, but the students staying in town attending Kentucky State University, also appreciate the work done by WalkBike.
In addition to the riverwalk, Frankfort also offers the Walk for Life program. Walk for Life has three color-coded wellness trails around historic Frankfort, the blue walk is 1.4 miles, the green walk is a mile, and the pink walk is 2.4 miles and includes the state capital. All of the color-coded walks form an easy loop, always using the safety of sidewalks.
Outside of the many walking opportunities, Frankfort also has an 18 hole golf course and sculpture park that sits on 10-acres featuring sculptures throughout the park.
And, of course, the capital of Kentucky has to have a bourbon distillery. Frankfort is home to the Buffalo Trace Distillery, a national landmark open to the public for tours and tastings.
Berea

- Percent of Senior Population: 13.2%
- Overall Population: 16,026
Berea is located in the middle of Kentucky, bordering the foothills of the Appalachian Mountains, adding to the city’s beauty. Berea is a welcoming town with a long history of diversity. It is home to the first and, for a long time, only interracial college in the south, Berea College.
But Berea College is not just unique for its rich historical value, but also because it is still a tuition-free college. Berea College students are required to work but never have to pay tuition, making it a much-desired school. The college adds a lot of life and vibrancy to the community.

And the one thing you will not find in this college town is a bar. Barea is a dry city, so alcohol is not sold or served here. However, Berea residents don’t need to drink to have fun; this city is the Folk Art Capital of the World and has an active arts and crafts community. Berea hosts three art and crafts festivals that bring in many tourists.
Avid outdoorsy retirees will love this area with its many outdoor adventure opportunities, such as Brushy Fork Park with about two and a half miles of easy trails, Anglin Falls featuring a short wooded hike, and West Pinnacle with a variety of nature trails, from easy hikes to more technical trails. And the nearby forest owned by Brea College, open to the public, has miles of trails, including some on Indian Fort Mountain.
Best of all Berea is one of the safer cities in Kentucky, which adds to this small town’s appeal.
Pikeville

- Percent of Senior Population: 12.8%
- Overall Population: 6,551
Pikeville is a small town on the eastern side of Kentucky, known as the city that moves mountains. This quiet town is ideal for retirees looking to buy a house in the mountains without breaking the bank.
Pikeville is a touristy town, especially during Hillbilly Days, one of the state’s biggest festivals. The town may be small, but it still offers a larger than expected dining scene with various global flavors, including Greek, Japanese, and Mexican cuisine.
Many retirees find Pikeville appealing for its many outdoor adventure opportunities, including zip-lining, the Hatfield and McCoy River trail, horseback riding, and hiking in Bob Amos Park.

And for those interested in history, Pikeville is home to the infamous feud between the Hatfield and McCoys. Besides taking a river tour, historic buffs can check out the Hatfield and McCoy landmark sites in the area too.
For those who enjoy live music, you never need to go far in Pikeville with the Wireless Arena in the middle of the town. The arena seats 7,000 and hosts several large music acts throughout the year.
Though Pikeville is a small town it does offer a local hospital, Pikeville Methodist Hospital.
Leave a Reply