21 Best Things to Do in Lexington, Kentucky - Wes Meets World ǀ Travel Blog

Lexington is famous for three things: Basketball, Horses, and Bourbon. The city is nestled in Central Kentucky, right in the heart of the Bluegrass State. It’s easy to get to with a regional airport and one hour by car in either direction from the metro cities of Louisville, KY or Cincinnati, OH. Whether you’re looking for an up-and-coming food scene, a weekend getaway for the family, or a jam-packed day at the horse races, Lexington, KY is the place for you.

The City of Lexington has a population of around 320,000 residents (as of 2019) and is steadily growing. It’s a college town at heart based on the prominent University of Kentucky’s medical programs and national basketball team champions. Beyond the University of Kentucky, it’s also a great place to raise a family or for young singles just starting out.

Lexington has that special “Southern Charm” you just can’t find in many other places. When you run into people you know throughout the city, you’ll hear a lot of “Thank You Ma’am” and “Bless Your Heart.” Even though I love to travel as much as I can, Kentucky always ends up being home. As the famous quote goes by Happy Chandler, “I never met a Kentuckian who wasn’t either thinking about going home or actually going home.”

If you’re interested in visiting Lexington, I’ve put together some of the best things to do while in the city. Everything from tasting bourbon to betting on the ponies, this list will keep you covered for a solid one-week trip in town. Let’s get started!

Things to Do in Lexington, Kentucky #1 – Tour the Bourbon Trail

Kentucky is famous for its bourbon. If you’ve ever had an “Old Fashioned” cocktail anywhere in the world, it all started right here in Kentucky. The state has a steep history in bourbon with Elijah Craig inventing the brown water by aging corn whiskey. He then opened Heaven Hill Distillery in Georgetown, KY in 1789 and the rest is history.

Today, there are 20 working bourbon distilleries in Kentucky that make up over 200 brands of bourbon. Set out on the Bourbon Trail by car to hop from distillery from distillery to join a walking tour, learn more about how bourbon is made, and have a sampling. If plan your visit ahead of time to Maker’s Mark distillery, you can even dip your own bottle in the famous red wax.

My personal favorite distillery to visit is Woodford Reserve in Versailles, KY (about 20 minutes outside Lexington, KY), but here is a list all the participating distilleries you can visit on the Bourbon Trail.

Things to Do in Lexington, Kentucky #2 – Catch a Basketball Game at Rupp Arena

Rupp Arena is located in the heart of Lexington’s downtown and hosts the University’s of Kentucky’s wildly popular basketball games. The arena was opened in 1976 and has been a staple of Lexington ever since. Rupp also holds conventions and major concerts throughout the year in the 23,500 seat area.

If you’re from Kentucky, you’re a UK Blue fan. That’s just the way it is. Some of the biggest fans will even say they “bleed blue.” The UK basketball team has won an impressive 8 NCAA Basketball Championships with 5 different coaches. The games are so popular that tickets can sometimes be a challenge to get your hands on, so plan your game visit in advance. The energy in Rupp Arena during a UK basketball game is electric, a must-visit event if you get the chance!

Photo Quinn Foster

Things to Do in Lexington, Kentucky #3 – Visit the Famous Kentucky Horse Park

While some states are famous for their theme parks for entertainment, here in Kentucky we’re broad of our theme park for horses. The Kentucky Horse Park is a working horse farm and educational theme park that hosts some of the world’s biggest and more notorious equine events, including the world-renowned Rolex Three-Day Event.

The park was opened in 1978 and provides tours throughout the week and admission to the International Museum of the Horse and the American Saddlebred Museum. During the summer, the park has horse-drawn tours and live equine presentations throughout the day. In the winter, the park hosts The Southern Lights where you can enjoy a holiday light show while driving through the park. There’s also a large area for camping and bringing your trailer for an overnight stay.

4 Savor the Local Coffee Scene

The coffee scene in Lexington has been steadily growing with boutique coffee shops popping up all around the city. As a freelance writer and blogger, the coffee shop is usually part of my daily office. If you’re a coffee junkie, there’s no shortage of places to stop in to get your caffeine fix and maybe even learn a little about the beans you’re drinking.

One of my favorite coffee shops in Lexington is Manchester Coffee Co. located on Manchester street in the distillery district. It has an industrial aesthetic to it with friendly baristas and coffee from all around the world. I’m also a fan of Lussi Brown Coffee Bar which turns from friendly neighborhood bar during the day to a cocktail bar at night serving coffee-inspired cocktails.

Another coffee shop that’s recently set up shop in downtown Lexington is Old School Coffee which moved into an old school house building (historic Dudley Square) which was constructed in 1881. The coffee shop serves up specialty drinks keeping the school house theme, like “The Student” and “The Superintendent,” along with seasonally inspired flavors.

Photo Old School Coffee

5 Travel the Kentucky Wine Trail

While it might not be quite as famous as the Bourbon Trail, the Kentucky Wine Trail offers an opportunity to sample local regional wines while taking in the views of beautiful Kentucky landscapes. There are 65 wineries that operate commercially in Kentucky where they focus on growing Cabernet Sauvignon, Chardonnay, and Cabernet Franc grape varietals.

Your first stop on the Kentucky Wine Trail should be to Equus Run Vineyards located in Midway, Kentucky (about 15 minutes outside Lexington). They’re open seven days a week where you can sip some wine in their stone-faced tasting room which was converted from a farm tool shed. They also have a tiered deck that overlooks the vineyards and put on seasonal events and concerts throughout the year.

The next stop on your Kentucky Wine Trail adventure is to Jean Farris located on Old Richmond Road in Lexington. This winery has large grounds where you can walk around and take in the sights and smells of Kentucky with a glass of wine in hand. Their motto is “Classic Wines with a Southern Drawl” and provide an on-site restaurant with traditional Southern Kentucky fare.

Photo Equus Run Vineyards

6 Drive Pisgah Pike Scenic Byway

Kentucky is full of beautiful horse farms, lush green fields, and old historic stonewall fences. There’s no shortage of incredible drives that can take your breath away when the light hits just right or the mist rises in the morning. One of those well-known scenic drives is located just outside Lexington on Pisgah Pike in Versailles, KY. This drive is great for anytime of the year, but spring or fall are the perfect times to enjoy the scenery.

If you’re looking to drive along this part of the Kentucky Scenic Byway, take Highway 60 (Versailles Road) away from Lexington’s downtown and keep driving until you pass Keeneland Racetrack on your right. About ten minutes past Keeneland, you’ll find The Kentucky Castle on your right sitting on a hill (yes, a castle!). Turn right at the castle, and you’ve found Pisgah Pike where you’ll drive along a windy two-lane road pasting famous Derby-winning horse farms and Southern churches.

7 Visit the Downtown Farmers Market

Every Saturday morning year-round (even in the colder months), Cheapside Pavilion in Downtown Lexington is bustling with its weekly farmers market. Lexingtonians from around the city head downtown to find fresh flowers, produce, local meat, freshly made pastas, pastries, artisan coffee, and even local Kentucky wine.

The busier months for the farmers market are April through October; however, the market still goes on during the winter with fewer vendors. In addition to its downtown location, the farmers market meets at various spots throughout the city on certain days of the week, including The Summit and Southland Drive.

Photo Lexington Farmers Market

8 Bet on the Horses at Keeneland Racetrack

Every good Lexingtonian knows that April and October each year is Keeneland season. This is when Lexington dresses up, heads to the races, and spends the day at the beautiful Keeneland racetrack doing one of Kentucky’s favorite pass times. Kentucky has a long tradition of horse racing. While the famous Kentucky Derby is found is held in Louisville every May and attracts people from all over the country, Keeneland is more of a locals track.

Keeneland was ranked #1 out of 65 thoroughbred racetracks in North America, based on a rating system given by the Horseplayers Associate of North America. It’s also designated as a National Historic Landmark and listed on the National Register of Historic Places.

No trip to Keeneland (or the Derby for that matter) is complete without trying a Mint Julep. This drink has been made famous as the cocktail of choice for the Kentucky Derby, but it’s adopted widespread across all of Kentucky. It’s a bourbon drink with mint, ice, and sugar. Serve it in a mint julep sterling silver cup and top with a sprig of mint, and you have the perfect drink for a day bettering on the ponies.

Photo Visit Lex

9 Visit Ashland (Henry Clay Estate)

Right in the heart of the Chevy Chase neighborhood in Lexington is Ashland, Henry Clay’s famous estate, which holds tours and events throughout the year. Henry Clay was a well-known statesman, and his plantation is preserved in the city as a National Historic Landmark. Every Christmas, the Henry Clay Memorial Foundation holds “A Kentucky Christmas at Ashland” where people can visit the plantation lit up with Christmas lights and holiday decorations.

Photo Visit Lex

10 Shop at The Night Market

The North Lime District of Lexington is an up-and-coming area of the city with renovation projects and new shops popping up every month. Every first Friday from May until December, the North Lime Community Development Corporation holds The Night Market where local vendors, food trucks, and businesses gather together to promote their goods and wares while reaching new audiences.

70% of the participating vendors live or work in the North Limestone neighborhood and 100% of the vendors are locally owned businesses. Heading down to The Night Market is a great way to contribute to the growing district while getting a feel for the Lexington vibe.

Photo KY for KY

11 See a Show at Manchester Music Hall

If you’re in the mood to see a show, Manchester Music Hall hosts world class musicians and bands from around the world. Located in Lexington’s Distillery District, Manchester is locally owned and operated.

The music hall is now held in what used to be the Old Tarr Distillery warehouse built in the 1800s. The building was part of the Ashland / Old Tarr Distillery campus and housed bourbon for many years. It was eventually purchased by Star Tool Company and then converted into Busters Billiards & Backroom, then Manchester in 2015. How cool to see your favorite band play live in an old distillery warehouse?

12 Bike the Legacy Trail

In an effort to increase Lexington’s trails and make downtown more accessible by foot (or bike), the Legacy Trail was built as a shared-used greenway trail connecting downtown Lexington with various nearby neighborhoods. While walking, running, or biking the trail, you’ll pass scenic areas of horse farms, pastures, and historic sites that make for a peaceful ride.

The trail is 12 miles long and stretches from Isaac Murphy Memorial Garden in Downtown Lexington to the Kentucky Horse Park campgrounds. It makes for a great way to get in a good workout while taking in the local scenery.

13 Take a Horse Farm Tour

No visit to the Bluegrass would be complete without a visit to one of the many famous working horse farms. There are about 450 farms in the region (150 in Lexington / Fayette County alone) making the area an ample opportunity to visit a piece of racing history. Take a guided tour along beautiful backcountry roads and snap a few pictures with the Derby-winning celebrities. You can reserve a seat on a guided tour or plan your own visits by calling the farms ahead of time for an appointment.

(Note that many farms only allow visitors through tour companies, so check ahead.)

One of the best farm tour companies in Lexington is Blue Grass Tours which operates farm tours from spring through fall. Their 3-hour “Horse Capital Tour” costs $40 and allows you to “indulge yourself in the incredible beauty of the Bluegrass” by visiting Keeneland Race Course and Old Friends Farm. Along the ride, enjoy picturesque horse country and historic Downtown Lexington.

14 Thursday Night Live

Every Thursday night from April to October, Downtown Lexington hosts a live band at Thursday Night Live. It’s one of the biggest events during the week for Downtown Lexington and happens rain or shine in the covered Fifth Third Pavilion. Along with live music, several vendors and food trucks pop up for beer, beverages, and snacks. Bring a chair and enjoy some music right in center of downtown!

15 Railbird Music Festival

Kentucky has an emerging music scene with the popular 3-day Forecastle Festival happening in Louisville every July, attracting growing crowds every year. The newest addition to Kentucky’s festival circuit is Railbird Festival which debuted in Lexington during 2019. The festival takes place on the grounds at the historic Keeneland Race Course as a celebration of music, bourbon, and equine experiences.

What’s a railbird you say? It’s a “horse racing enthusiast known for sticking close to the action, hanging on the rail as each contender comes barreling down the track.”

The debut festival brought some major headliners, including Brandy Carlisle, Hozier, and Tyler Childers, and is bound to continue attracting big names. If you plan to visit, make a weekend of it by staying downtown, taking a bourbon tour, and enjoying the live music all weekend long.

Photo MusicFestNews.com

16 Spend the Night in a Tree House

How would you like to spend the night in a tree house? Well, with The Canopy Crew, you can make that dream a reality! This company has built some of the most unique livable tree houses where you can rent for the night to watch the stars and take in the remote beauty of Kentucky’s Red River Gorge.

The Red River Gorge is a canyon system located in Eastern Kentucky. It has an area of around 29,000 acres and is located in the Daniel Boone National Forest.

One of The Canopy Crew’s tree houses (The Looking Glass) features a 360 of the forest around you, fully stocked kitchen, bridge to check out the sights, and a deck to kick back and relax. It makes for the perfect weekend adventure while visiting the Bluegrass State.

Photo The Canopy Crew

17 Ice Skating at Triangle Park

New York City might be famous for its ice skating rink with a view of the Rockefeller Center Christmas Tree; however, Lexington boasts its own little pop-up ice skating rink right in the heart of downtown.

Every Christmas Season right after Thanksgiving, the rink comes to life letting kids and families skate around the ice at Triangle Park. The rink isn’t just for kids as it makes a perfect wintery date night, too. The park’s café offers snacks and hot chocolate, along with bourbon drinks for the adults (you can’t have ice skating in Kentucky without bourbon, right?).

18 Go on a Downtown Ghost Walk

Did you know Lexington has quite a bit of its own ghost history? Patti Star with Ghost Walk of Lexington will gladly take you a tour of downtown where you can learn more in depth history of the area through the storytelling of its ghostly tales.

According to her website, “Her tales will include hauntings from a murder, curse, and other macabre happenings while entertaining you with intriguing history. Patti also brings her iPad where she shows pictures of ghost apparitions that have been captured while walking on the tour.”

The tour around historic Gratz Park in Downtown Lexington is bound to put you in the “Fall Spirit.” Every time I go on this tour, I grab a hot coffee, put on some comfortable walking shoes (there’s quite a bit of walking involved), and bundle up with a coat to re-live the stories. I’ve actually learned quite a bit about Lexington’s history as a result.

19 Tour Jack-o-Lanterns at Transylvania

Every year, Transylvania University hosts its annual “Pumpkinmania” featuring hundreds of brightly-lit, carved pumpkins on the school’s Old Morison Building’s historic steps.

While the pumpkins stay lit for days leading up to Halloween, the school hosts an official event with food trucks, games for kids, and an official lighting of the pumpkins. It makes for a great way to get in the Halloween spirit!

Photo Transy.edu

20 Crave Food Festival

Lexington has become a growing culinary scene with an eclectic mix of restaurant varieties across the city. The city is home to some top chefs like Jonathan Lundy (chef at Lexington’s Corto Lima Latin infusion restaurant) and Ouita Michaels (known for her Southern cooking flare at restaurants like The Windy Corner and Zim’s Cafe).

As a result of Lexington’s rise of foodie groups, the Crave Food Festival was born as a way to feature the city’s variety of dining establishments. The festival spans over a weekend with 50+ featured restaurants & food trucks, along with local music and bands, classic car show, and cook-offs.

21 Eat Up the Downtown Culinary Scene

As mentioned, Lexington has experienced a growing culinary scene over the last few years. One of the most concentrated areas of excellent restaurants is right in the city’s downtown. Centered around the downtown’s covered Fifth Third Pavilion (where the farmers market takes place) is Corto Lima (Latin infusion), Tony’s of Lexington (steakhouse), Carson’s Food & Drink (American), and Jeff Ruby’s (steakhouse).

One of the best parts of downtown is that it is all very walkable. Just park your car and head out to sample some of Lexington’s best restaurants. After dinner, try some cocktails at Ona (cocktail bar featured Esquire Magazine’s “best bars in America”) or West Main Crafting Co. for some top-shelf mixologist-made beverages. Of course, I recommend getting the bourbon.

Photo Smiley Pete Publishing

Are You Ready to Visit Lexington, KY?

Right in the heart of the Bluegrass, Lexington provides stretches of breathtaking horse farms, tasty sips of Kentucky bourbon, and nationally recognized basketball champions. I always say Lexington is known for its “horses, bourbon, and basketball.” What else could you want?

Have you been to Lexington, KY? What was the most favorite part of your visit? What else do you recommend doing while in Lexington? Drop your answers in the comments below!