Derby, Star Wars, Cinco de Mayo: Best things to do in, around Lexington this weekend

Matt Wickstrom
·5 min read

Have an upcoming weekend event to list? Please send details a week in advance to Bsimms@herald-leader.com and jpatton1@herald-leader.com .

Here is a Lexington list and guide of the best weekend events around Central Kentucky on Friday, Saturday and Sunday if you are bored and need things to do including family-friendly events, live music concerts, classical music concerts, comedy shows, free events, University of Kentucky games, singing concerts, May the Fourth Star Wars event, Cinco de Mayo celebration and Kentucky Derby parties and race watching events.

Poor Man’s Harlan County Derby Eve Party at Two Keys Tavern

The 50th annual Poor Man’s Harlan County Derby Eve Party will take place at Two Keys Tavern on May 3 at 6 p.m. with a silent auction, live music and more. $25. 385 S Limestone. Facebook.com.

Blue Jeans, Boots & Bulls at Bluegrass Stockyards

The Bluegrass Stockyards will host its second annual Blue Jeans, Boots & Bulls Kentucky Derby Eve party benefiting the Kentucky Children’s Hospital NICU, Timber’s Grateful Companions and Old Friends on May 3 from 5:30-11:30 p.m. Activities include a silent auction, live music, dinner and more. From $100. 4561 Iron Works Pike. Eventbrite.com.

UK Baseball vs. Arkansas at Kentucky Proud Park

The UK Baseball Cats will take to the diamond for a three-game set with the Arkansas Razorbacks at Kentucky Proud Park on May 3 at 6:30 p.m., May 4 at 2 p.m. and May 5 at 1 p.m. $7-$25. 510 Wildcat Ct. UKAthletics.com.

Comedian Lee Cruse at Comedy Off Broadway

Comedian and television host Lee Cruse, whose “The Lee and Hayley Show” just moved to FOX 56, will perform at Comedy Off Broadway on May 3 at 7 p.m. and May 4 at 6 and 8:30 p.m. $15-$18. 161 Lexington Green Cir #C4. ComedyOffBroadway.com.

Comedian Kathy Griffin at the Lexington Opera House

Comedian Kathy Griffin will perform at Lexington Opera House.
Comedian Kathy Griffin will perform at Lexington Opera House.

Emmy and Grammy Award-winning comedian Kathy Griffin will bring her “My Life On The PTSD-List” tour to the Lexington Opera House on May 3 at 7:30 p.m. From $50. 401 W Short St. CentralBankCenter.com.

After stalled career & cancer, Kathy Griffin is still standing (up), coming to Lexington

“The Three Musketeers” at the Leeds Center

The Leeds Center for the Arts in Winchester will host performances of “The Three Musketeers” from May 3-12, with this weekend’s shows coming on May 3 and 4 at 7:30 p.m. and May 5 at 2:30 p.m. $18-$22. 37 N Main St, Winchester. Eventbrite.com.

Derby Day at Keeneland, tailgate at The Hill

If you can’t make it to Churchill Downs, you can enjoy the Kentucky Derby Day atmosphere at Keeneland.
If you can’t make it to Churchill Downs, you can enjoy the Kentucky Derby Day atmosphere at Keeneland.

Watch the Kentucky Derby at Keeneland, post time at 6:57 p.m. Gates open at 10 a.m., bring your own seating or sit in the grandstand and public seating areas. The Hill also is open for free tailgating with live music, food trucks, betting windows and more. General admission, $7-$10, children under 12 free, no outside food or drink allowed inside the track gates. 4201 Versailles Rd. Keeneland.com

Heather Clark of Frankfort sips her drink on Kentucky Derby day at Keeneland Race Course in Lexington, Ky., Saturday, May 6, 2017.
Heather Clark of Frankfort sips her drink on Kentucky Derby day at Keeneland Race Course in Lexington, Ky., Saturday, May 6, 2017.

African-American Heritage & Horse Day in Paris

Celebrate African-American contributions to the Equine Industry on May 4 with a block party and fish fry hosted by the Paris Westside Neighborhood Association (PWNA.) Activities include cornhole, bingo, a stick horse race, a fedora-making contest, the presentation of a Snow Fields portrait to the Hopewell Museum, and more. 400 Williams St, Paris. Facebook.com.

Kentucky Derby Watch Party, Live Music at Manchester Music Hall

Manchester Music Hall will be rocking all Derby Day on May 4 with a watch party beginning at noon that will include a hat competition at 5 p.m. and live post-race music from Tyler Bryant & The Shakedown. $18-$75. 899 Manchester St. ManchesterMusicHall.com.

May the Fourth at McConnell Springs

May the Fourth Be With You Star Wars celebration at McConnell Springs May 4, 2023.
May the Fourth Be With You Star Wars celebration at McConnell Springs May 4, 2023.

Dress in your Jedi, Wookie or Mandalorian costume for the annual May the Fourth Star Wars celebration, 1-4 p.m. at McConnell Springs, with activities along the trail, food trucks Mr. Gyro’s, Bert’s SpeakCheezy, Bryan’t Red Hot Dogs, Pasta Garage, Old Kentucky Kettle Corn, Cloud Candy, Kona Ice, Tin Can Coffee, West 6th Brewing, Wise Bird Cider Co., performances, music, a photo booth, Star Wars-themed printmaker. Free. 416 Rebmann Lane. Facebook.com

Lexington Farmers Market downtown, on Southland Drive

Lexington Farmers Market will have spring greens, plants, bread, cheeses, fruits and vegetables downtown in Tandy Centennial Park on Main Street April 27 8 a.m. to 2 p.m. and on Southland Drive 10 a.m. to 2 p.m. Free. Lexingtonfarmersmarket.com

Grayson Jenkins Concert at The Burl

Muhlenberg County-born, Nashville-based country singer Grayson Jenkins will return to Lexington for a concert at The Burl on May 4 at 8 p.m. with Thomas Csorba. $15. 375 Thompson Rd. TheBurlKy.com.

Maker’s Market at The Void Sake Company

The Void Sake Company will host its first-ever maker’s market featuring handmade jewelry, soap, art, ceramics and more on May 5 from 12-5 p.m. 819 National Ave #120. Facebook.com.

Rosé and Cheese Pairing Class at Harkness Edwards Vineyards

Celebrate Mother’s Day with a special Rosé and cheese pairing class at Harkness Edwards Vineyards in Winchester on May 5 at 1:30 and 3:30 p.m. $39. 5199 Combs Ferry Rd, Winchester. Facebook.com.

“Circle And Square” at the Lexington Children’s Theatre

The Lexington Children’s Theatre will host performances of “Circle And Square” on May 5 at 2 and 4:30 p.m., with the latter show being a sensory friendly affair. $10-$15. 418 W Short St. LCTOnStage.org.

Central Kentucky Concert Band at the Lexington Opera House

Horn soloist Melanie Kjellsen will perform with the Central Kentucky Concert Band.
Horn soloist Melanie Kjellsen will perform with the Central Kentucky Concert Band.

The Central Kentucky Concert Band will perform “Cornucopia” — its final concert of the 2023-2024 season — featuring horn soloist Melanie Kjellsen at the Lexington Opera House on May 5 at 3 p.m. Free. 401 W Short St. CKCB.org.

May Block Party on Southland

Local LEX Market will be at 439 Southland Drive 10 a.m. to 4 p.m. on May 5, with local makers, artists, vendors, food trucks and a margarita truck for Cinco de Mayo. Locallexmarket.com

Old Friends 19th Annual Homecoming

Old Friends racehorse retirement farm will host a homecoming May 5 noon to 4 p.m. with auctions of racing memorabilia, collectible halters, equine art, jewelry and more. Proud Mary catered BBQ, music and tours. Tickets on secure.givelively.org $23-$50, kids 12 and under free. 1841 Paynes Depot Rd. in Georgetown. oldfriendsequine.org