Experience an Exciting May in Lexington: Your Ultimate Guide to May Concerts and Live Events

Spring has fully blossomed in Lexington, and with it comes a vibrant lineup of concerts and live performances that promise to make your May unforgettable. Whether you're a fan of comedy, rock, country, or orchestral music, Lexington's event calendar is packed with diverse entertainment options. Get ready to mark your calendars, gather your friends, and immerse yourself in the lively arts scene that makes Lexington such a special place to enjoy live entertainment.

Kick Off May with Comedy and Country at Lexington Opera House

The month begins with a bang as the Lexington Opera House hosts the hilarious Theo Von on May 1st and 2nd. Known for his sharp wit and engaging storytelling, Theo Von's performances are a must-see for comedy lovers. Tickets are available at Theo Von’s event page. Not far behind, on May 5th, Amy Grant will take the stage, offering a soulful blend of gospel and pop that has captivated audiences for decades. Secure your seat at Amy Grant’s concert.

Comedy Continues with Patrick Warburton and Jessica Kirson

Comedy fans will enjoy the stand-up talents of Patrick Warburton performing at Comedy Off Broadway on May 11th. Known for his roles in popular TV shows, Warburton’s stand-up promises plenty of laughs. For more details, visit Patrick Warburton’s page. Later in the month, Jessica Kirson brings her hilarious act to Lexington on May 29th and 30th, with multiple shows that are sure to sell out. Grab your tickets early at Jessica Kirson’s ticket site.

Rock and Roots: Live Music at Manchester Music Hall and The Burl

Mid-May is packed with high-energy live music. On May 7th, The Burl hosts Drake Milligan, a country artist promising an electrifying performance—get your tickets at Drake Milligan’s event page. Later, on May 16th, Rupp Arena welcomes Phil Wickham, whose contemporary Christian music offers a soulful escape. Check out the details at Phil Wickham’s concert.

For fans of indie and alternative sounds, The Burl features Molly Tuttle & Maggie Rose on May 16th, blending bluegrass with modern Americana—more info at Molly Tuttle & Maggie Rose. Also, the same night, Buckcherry will rock Manchester Music Hall, delivering their signature edgy rock sound. Tickets are available at Buckcherry’s page.

Classical and Symphonic Highlights

For those seeking a more refined musical experience, the Lexington Philharmonic & Lexington Singers present their "Symphony of Sound" at the Lexington Opera House on May 15th. This orchestral event is perfect for classical music enthusiasts—find tickets at Symphony of Sound. Additionally, Mac McAnally performs on the same date, offering a blend of country and Americana at the Opera House—reserve your spot via Mac McAnally’s page.

Comedy and Alternative Acts to Keep You Laughing

Throughout May, Comedy Off Broadway continues to deliver top comedic acts. Notably, Derrick Stroup performs multiple nights from May 7th to 17th, with tickets available at Derrick Stroup’s page. Also, Shapel Lacey on May 21st and Amber Autry on May 1st-3rd bring their unique humor to Lexington’s comedy scene. For tickets, visit the respective links provided.

Special Events and Unique Performances

Music fans can look forward to Ingested, a metal band performing at Manchester Music Hall on May 9th, with tickets at Ingested’s page. The same venue hosts Christone Kingfish Ingram on May 13th, a blues artist delivering soulful melodies—more info at Kingfish Ingram’s event. For a nostalgic trip, The Sixties Show offers a lively homage to the 1960s at Lexington Opera House on May 21st; details are at The Sixties Show.

Other notable events include Sidewalk Prophets, a contemporary Christian band performing at Heritage Hall on May 29th, with tickets at Sidewalk Prophets. For alternative and hard rock fans, CKY plays on May 17th, and more details are available at CKY’s page. Metalcore band Demon Hunter performs at Manchester Music Hall on May 15th, with tickets at Demon Hunter.

Closing the Month with Diverse Acts

As May draws to a close, the lineup continues with Ingested, and the energetic band Tigers Jaw at The Burl on May 29th. Check out Tigers Jaw for more information. The month ends with the combined talents of Fit For A King, Invent Animate, Ten56 & Acres at Manchester Music Hall on May 31st—tickets are available at Fit For A King & Co..

Plan Your May Concerts Today!

With such an incredible variety of performances, May in Lexington is the perfect time to explore live entertainment. Be sure to check out concert.lexingtontickets.org/may/ for more details, ticket links, and to secure your spot at your favorite events. Whether you're into comedy, rock, classical, or country, Lexington’s vibrant arts scene is ready to provide unforgettable experiences. Don’t miss out—get your tickets early and enjoy an incredible month filled with music, laughter, and entertainment!