As May rolls into the Bluegrass region, Lexington and its surrounding cities like Harrodsburg, Richmond, and Frankfort come alive with festivals, outdoor fun, and cultural events. It’s the perfect time to get outside and enjoy everything Central Kentucky has to offer. Whether you’re a long-time resident or planning a weekend getaway, there’s no shortage of exciting things to do in May 2025. Here’s a look at some of the can’t-miss events and happenings in and around Lexington this May. 1. Mayfest Arts Fair (Lexington) Kick off the month with the annual Mayfest Arts Fair in Gratz Park. Taking place on May 10–11, this free event celebrates the arts with live music, food vendors, and over 100 local and regional artists showcasing their work. It’s a family-friendly event that also features kids’ activities, performances, and hands-on art experiences. 2. Horse Capital Marathon & Half Marathon (Lexington) For runners and fitness enthusiasts, the Horse Capital Marathon and Half Marathon is scheduled for May 18, 2025. This race takes you through the scenic Kentucky countryside, past horse farms and rolling hills. It's one of the most beautiful courses in the region and a great way to experience the spirit of Lexington on foot. 3. Kentucky Mountain Laurel Festival (Pineville – Day Trip Option) If you're up for a scenic drive, the Kentucky Mountain Laurel Festival in Pineville (May 22–25) is a time-honored tradition featuring a grand parade, beauty pageants, live music, and craft vendors. While it’s a bit outside Lexington, it makes for a fantastic day trip filled with local charm and southern hospitality. 4. Memorial Day Weekend Events (Various Locations) Memorial Day weekend in Lexington and surrounding towns is packed with family-friendly events. Look out for: Local parades honoring veterans Community cookouts and picnics Fireworks displays in select towns Jacobson Park often hosts a special Memorial Day event with food trucks, games, and live music, making it a favorite for families. 5. Keeneland May Special Events While the spring meet ends in April, Keeneland often hosts special events in May such as charity galas, food and wine tastings, and private tours. Check their event calendar for unique opportunities to enjoy the historic racecourse in a different light. 6. Picnic at the Park Series (Frankfort) Every Thursday in May, the city of Frankfort holds its Picnic at the Park concert series at Ward Oates Amphitheatre. Bring a blanket or lawn chair, grab lunch from a local vendor, and enjoy live music in a scenic riverside setting. It’s a relaxed way to enjoy a midday break and support local musicians. 7. Lexington Farmers Market (Downtown & Southland Drive) Throughout May, you can catch the Lexington Farmers Market at multiple locations: Downtown on Saturdays Southland Drive on Sundays Various weekday pop-ups It’s one of the best ways to enjoy fresh produce, handmade crafts, local honey, baked goods, and more. Plus, live music and cooking demos often make it a lively experience. 8. EKU Center for the Arts Performances (Richmond) The EKU Center for the Arts continues to bring national tours and top-tier entertainment to Central Kentucky. In May 2025, expect performances ranging from Broadway musicals to stand-up comedy. Check their schedule early—shows tend to sell out quickly. 9. Bourbon Tastings and Distillery Tours May is the ideal month for a bourbon trail adventure. Enjoy the weather with outdoor tours at popular distilleries like: Buffalo Trace in Frankfort Town Branch in Lexington Wilderness Trail in Danville (just a short drive away) Many offer seasonal tasting experiences, cocktail-making classes, and picnic-friendly outdoor spaces. 10. Arboretum Events and Nature Walks The University of Kentucky Arboretum is in full bloom in May, offering walking trails, kids’ programs, and community gardening events. It’s a peaceful way to spend the day outdoors while learning more about local plants and ecosystems. Final Thoughts May in Lexington is all about enjoying the beautiful weather, vibrant culture, and rich traditions of the region. With something happening nearly every weekend—from art fairs to bourbon tastings—there’s no better time to get out and explore what Central Kentucky has to offer. Whether you’re looking for adventure, family fun, or a relaxing afternoon in the park, you’ll find it right here in the heart of the Bluegrass.