The start of summer is always an exciting time in Lexington, but this June is going to be one for the books. A jam-packed calendar of special 250th Anniversary events paired with the city’s unique year-round attractions makes for one big party in the Bluegrass.
Here’s just a few of the things you can do when you invite your friends and family to kick it in Lexington this June.
1. Celebrate the City
Pictured here: African American Heritage walking tour
Lexington is celebrating its 250th Anniversary with citywide special events and programming throughout 2025. Activities range from entertaining to educational, and more are being added every day so be sure to check the official Calendar of Events for the most up-to-date info.
As of today, The Big Ass Bourbon Tasting—featuring a flight of four bourbons, food, live music, giveaways and more—will be held at LexLive on Wednesday, June 11. And the 2025 Tea and Talk at Waveland: “The Story of the Blunderbuss and Charlotte Mentelle” is happening on Saturday, June 14.
Get to know Lexington at your own pace with our self-guided African American Heritage Walking Tour and Downtown Walking Tour. They’ll direct you toward dozens of points of interest around town that will give you a deeper appreciation for the people and events that have shaped the city over the last two and a half centuries.
2. Catch Some Live Music
Pictured here: Railbird Festival
If music is your thing, you’re going to love Lexington in June. Festival season will be rocking, and venues big and small will be hosting local and touring artists of all genres. Lainey Wilson and Jelly Roll are headlining a stacked lineup at this year’s Railbird Festival at Red Mile Racetrack and Spirit In the Bluegrass Music Fest is back at the Kentucky Horse Park. Intimate performances from up-and-coming artists can be seen almost daily at The Burl, and Thursday Night Live in downtown’s Tandy Park is always a good time.
You can also catch Ryan Adams and The Wallflowers at the Lexington Opera House. And Billy Strings is headed to Rupp Arena for two nights.
3. Savor Seasonal Flavors
Pictured here: Granddam at The Manchester
June means even more fresh local ingredients than usual on menus at Lexington’s eclectic array of eateries. Granddam, the in-house restaurant of The Manchester Hotel, serves elevated Appalachian cooking. Lockbox, Corto Lima and ItalX are known for creatively incorporating homegrown ingredients. And you can get a taste of Sri Lanka at James Beard Award-nominated Chef Sam Fore’s Tuk Tuk Snack Shop on Lexington’s Southside. SoulFeast Week, a 10-day celebration of Black culinary culture in Kentucky, highlights the delicious work of local Black farmers, chefs, and Black-owned restaurants.
Can’t decide where to start? Bites of the Bluegrass can take you on a foodie tour of some of the city’s best eateries and you can try a little of everything with a side of local history.
4. Sip On Bourbon, Craft Beer & Cocktails
Pictured here: Fresh Bourbon
Beneath Lexington’s rolling bluegrass hills, a rare limestone formation filters natural spring water for the world’s finest bourbon, fueling a magical culture of creativity and innovation that we call Bourbonland. This June, experience that culture at 18 nearby bourbon distilleries and our world-class bourbon bars.
Burl Brew and West Sixth Brewing pour housemade beers best enjoyed in their ample outdoor seating areas. Lost Palm is a tropical rooftop bar in the Distillery District with a flamboyant tiki vibe. And, when you’re ready to wind down, late-night drinks in the moody ambiance of Ona is always a relaxing way to end the evening.
5. Explore the Bluegrass
Pictured here: Horseback Riding at the Kentucky Horse Park
Not too hot. Not too cold. June is just right for getting outside and exploring the Bluegrass. Raven Run Nature Sanctuary is a 734-acre preserve just minutes from downtown Lexington. The Arboretum, the State Botanical Garden of Kentucky, is another great spot to see the Bluegrass blossom.
One of Lexington's top outdoor attractions, Boone Creek Outdoors features six zip lines, three sky bridges, a rappel, a spiral, and a floating staircase—all suspended from the magnificent hardwood trees of Boone Creek Gorge. Or head down the Kentucky River with Kentucky By Paddle. You can rent one of their standup paddleboards or bring your own paddlecraft for one of their guided group outings.
Of course, no trip to the Bluegrass is complete without some equine action. Set your alarm early and catch the morning workouts of impressive Thoroughbreds at Keeneland. Go behind the scenes at area horse farms and facilities with the help of Horse Country Tours. And get up close and personal with dozens of horse breeds at the 1200-acre Kentucky Horse Park.
6. Show Your Pride
Pictured here: Lexington Pride Festival
Lexington is home to a large, vibrant LGBTQ+ community and consistently ranks among the best cities in America for LGBTQ+ rights. Every June, our welcoming nature is on full display during the Lexington Pride Festival, Central Kentucky's premiere LGBTQ+ celebration. Expect live entertainment, a diverse array of vendors, food, informational booths, and activities at this outdoor event.
Lex Lez Night is a gathering for women-loving women that takes place the second Thursday of every month at Lussi Brown Coffee Bar and Crossings Lexington. Other local LGBTQ+ businesses and organizations are often featured during the event.
Check out our LGBTQ+ Guide to Lexington for more spots around town where you can connect with this invaluable part of the city’s culture.
7. Tap Into the Creative Culture
Pictured here: The Horse on High Knoll Mural
Lexington buzzes with creative energy. Tap into that vitality this June by immersing yourself in the city’s inspiring culture. The Lexington Mural Challenge will guide you to some of our best public art. Equal parts glassblowing studio, art gallery, and speakeasy, Trifecta: Glass - Art - Lounge is a one-stop cultural experience. Or grab a drink from the bar and browse the gallery of contemporary art at 21c Museum Hotel.
A historic hub for performing arts of all sorts, the Lexington Opera House is a revitalized downtown venue dating back to 1886. You can catch comedians Fortune Feimster and Eddie Griffin there this June.
