Derby parties, Mother’s Day celebrations: Don’t miss these Lexington events in May
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Between Kentucky Derby watch parties, outdoor festivals and Mother’s Day events, there are plenty of events to add to the calendar for May.
Here’s a summary of events you don’t want to miss this month in Central Kentucky, including live performances, sporting events, outdoor festivals and much more.
Black Violin concert
The Grammy-nominated duo Black Violin will perform at the Lexington Opera House on May 1. Artists Wil Baptiste and Kev Marcus combine to form classical violin music with a hip-hop pulse.
The group will be stopping in Lexington for the Full Circle Tour. The Central Bank Center’s website says the tour, “captures the essence of returning to where it all began — transformed and reimagined.”
Show time is 7:30 p.m., and tickets are on sale for as low as $30.50 plus fees.
Shinedown concert
Multi-platinum rock band Shinedown will perform at Rupp Arena on May 2. Artists Beartooth and Morgan Wade will also perform at the concert, scheduled to start at 7 p.m.
Shinedown has more than 6.5 billion global streams, 21 No. 1 rock hits and 10 million albums sold worldwide, all of which have platinum or gold certification, according to the Central Bank Center.
Tickets are on sale for as low as $29.50 plus fees. $1 from every ticket sold will benefit Musicians On Call, an organization that brings live and recorded music to patients, families and caregivers in healthcare environments.
Derby Event: Run for the Roses
There will be a family-friendly, Kentucky Derby-themed event at Hamburg Pavilion May 2-3. The event will feature horse meet and greets, face-painting, balloon creations and a derby-themed magic show.
Attendees can also sip on junior lemonade julep and craft a lucky horseshoe.
The event will be held at 2308 Sir Barton Way #190, the previous iLoveKickboxing space next to Victoria’s Secret and behind My Salon Suite and Dollar Tree. It is free to attend.
Kentucky Derby watch parties
Those not able to make it to Churchill Downs for the Kentucky Derby can take in the greatest two minutes in sports at Lexington’s race tracks.
Keeneland will host a derby watch party beginning at 10 a.m. on May 3. There will be live performances from The Jenkins Twins, Joslynn & The Sweet Compression and Vinyl Richie in the Paddock between noon and 6:30 p.m. before the horses report to the post at 6:57 p.m. There will also be a hat contest at Milliners Corner and several activities for children, including face painting, pony rides, children’s games and crafts, at Keeneland’s first floor clubhouse
General admission tickets are $10.
The doors at Red Mile open at 10:30 a.m., and a buffet for guests will start one hour later. There will also be a teller on site for betting advice, a full bar and several TVs for people to watch the races.
Reservations are by table only, and the only options available are six-person tables for $360. However, reservations are not require,d and walk-ins will be accepted if space allows.
Mama, I’m A Big Girl Now
Tony Award-winning and nominated actresses will take the stage at the Lexington Opera House on May 7 for Mama, I’m A Big Girl Now. The show will feature Tony Award Winner Marissa Jaret Winokur, Tony nominee Kerry Butler and Lexington native and Tony nominee Laura Bell Bundy.
“I really care about this show because it’s my hometown and the Opera House was the very first theater I ever performed in,” Bundy said in a news release.
Winokur, Butler and Bundy have combined for more than 16 Broadway shows and 200 television appearances, according to the Central Bank Center. The New York musical is about teenage performers who turned into stars.
Tickets are on sale for as low as $59.50 plus fees. Showtime is scheduled for 7 p.m.
Pink Floyd Laser Spectacular
Pink Floyd fans won’t want to miss the Pink Floyd Laser Spectacular happening at the Lexington Opera House on May 10. Presented by Paramount, the show uses cutting-edge effects and high-powered lasers to enhance the experience of listening to Pink Floyd’s hits live.
Tickets are on sale for as low as $33.50 plus fees. Showtime is scheduled for 8 p.m.
Mayfest Arts Fair
The Mayfest Arts Fair will return to Gratz Park on Mother’s Day weekend, May 10-11. The family-friendly art fair will feature up to 100 vendors, performances by musicians and dancers, food concession vendors and family activities.
Mother’s Day events
People looking to treat mothers to a special day will have many opportunities to do so.
Wildside Winery is hosting a Mother’s Day Spring Market at its location on Troy Pike in Versailles. Mothers will get to drink wine, shop for handcrafted goods from local art vendors and enjoy live music. The free event will be on May 10 and 11.
At Marriott Lexington Griffin Gate Golf Resort & Spa, there will be a Mother’s Day Brunch featuring a variety of appetizers, main courses and desserts on May 11. Tickets for the brunch cost $30 for kids 9 or older and $70 for adults. Kids 8 and younger are free.
There will also be several events celebrating mothers at Shaker Village of Pleasant Hill in Harrodsburg from May 9-11. Events include an Evening at the Amphitheatre, the Mother’s Day Farm and Garden Market, an Introduction to Essential Oils workshop, a Cornhusk Flowers workshop and a Mother’s Day Dinner at The Trustees’ Table.
Tickets must be purchased for the workshops, and reservations must be made for the dinner, while access to the farm and garden market is included with a general admission ticket.
West Sixth Beer Garden Pop-Up
Amid Lexington Craft Beer Week, there will be the West Sixth Beer Garden Pop-Up at Woodland Park on May 15. The West Sixth team will pour fresh beer from their draft trailer, and the temporary beer garden will also feature food trucks, background music, lawn games and activities for families.
Monster Jam
Monster Jam will make its return to Rupp Arena on May 17. The thrilling and action-packed monster truck show will feature some of the most popular trucks in the world, like Grave Digger, El Toro Loco and Sparkle Smash.
There are two shows on May 17 — one at 1 p.m. and another at 7 p.m. Tickets are on sale for as low as $28.20 plus fees for the matinee show and $23.50 for the evening show.
StreetFest 2025
People of all ages can celebrate streets as a shared space at StreetFest 2025 from 10 a.m. to 1 p.m. on May 17. The event will be held at 540 E. Third Street, and people will be able to ride, scoot, skate or just walk freely on the road.
The purpose of the event is to promote complete streets that are designed to be safe for all modes of transportation.
There will also be games, bouncy houses, vendors, food and fun for families.
Chamber Music Festival of the Bluegrass
Shaker Village of Pleasant Hill will host its 17th annual Chamber Music Festival of the Bluegrass on May 24 and May 25. There will be four classical music concerts in the village’s Meadowview Barn throughout the weekend.
One of the performances includes composer David Ludwig, the Dean of Music at The Juilliard School. Ludwig will also host a complimentary educational lecture Sunday afternoon.
General admission tickets are sold separately per show and range from $48-$75 per person.
Sleeping Beauty ballet
The Kentucky Ballet Theatre will present two shows of Sleeping Beauty at the Lexington Opera House on May 24 and 25. Alisha Hill will star as princess Aurora, who must sleep until a prince’s kiss awakens her.
Hill joined the theater in 2018 and has played various roles. Jorge Emilio Pena will dance the role of the prince, Alexandra Montgomery will dance the role of fairy Carabosse and Karen Sakamoto is the Lilac Fairy.
Tickets are on sale for both shows for as low as $33 plus fees. Show times start at 2 p.m.
Railbird kickoff
The popular early summer music festival Railbird will kick off May 31 on the infield of Red Mile. Headliners of the festival’s first day are Lainey Wilson, Bailey Zimmerman and Shaboozey.
Headliners for June 1’s show are Jelly Roll, Riley Green and The Red Clay Strays. There are more than 30 acts scheduled over two days.
A variety of ticket options are available, including single-day passes starting at $150 and two-day passes starting at $250. There are also GA+, VIP, platinum, superfecta and cabana tickets available.
This story was originally published May 1, 2025 at 9:08 AM.
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