Entertainment events in Lexington

Check out happening entertainment events all around Lexington, KY

Lexington Pride Festival 2026

 Sat, 30 May at 12:00 pm Oliver Lewis Way , (South Broadway to High Street), Lexington, KY, United States, Kentucky 40507

Theo Von at Lexington Opera House

 Fri, 01 May Lexington Opera House

Disney On Ice at Rupp Arena

 Fri, 01 May at 10:30 am Rupp Arena

Monster Jam

 Fri, 19 Jun at 07:00 pm Rupp Arena At Central Bank Center USD 25 to 75

Monster Jam at Rupp Arena

 Sat, 20 Jun at 02:00 pm Rupp Arena

Mayfest Arts Fair Presented by Central Bank

 Sat, 09 May at 10:00 am Gratz Park Historic District

Flower Power Dyes at The Lexington Pride Festival

 Sat, 30 May at 12:00 pm Lexington Pride Festival

Ragnar Road Bourbon Chase 2026

 Fri, 02 Oct at 06:00 am Lexington, KY

Disney On Ice presents Jump In!

 Fri, 01 May at 07:00 pm Rupp Arena

Kentucky Three-Day Event - 3 Day Grounds Pass

 Thu, 23 Apr at 07:00 pm Rolex Stadium at Kentucky Horse Park

David Cross at Comedy Off Broadway

 Fri, 24 Jul at 07:00 pm Comedy Off Broadway

Kentucky Three-Day Event - 4 Day Grounds Pass

 Wed, 22 Apr at 07:00 pm Rolex Stadium at Kentucky Horse Park

2026 Defender Kentucky Three Day Event - Saturday at Alltech Arena at Kentucky Horse Park

 Sat, 25 Apr at 09:00 am Alltech Arena at Kentucky Horse Park

New Found Glory

 Sun, 10 May at 07:00 pm Manchester Music Hall

Patrick Warburton at Comedy Off Broadway

 Mon, 11 May at 07:00 pm Comedy Off Broadway

Wilco

 Fri, 17 Jul at 11:00 pm The Burl

Phil Wickham - Lexington, KY

 Sat, 16 May at 07:00 pm Rupp Arena

Amy Grant at Lexington Opera House

 Tue, 05 May at 07:30 pm Lexington Opera House

The Steeldrivers in Lexington

 Sat, 13 Jun at 07:00 pm Kentucky Horse Park

Marty Stuart and His Fabulous Superlatives

 Wed, 15 Jul at 07:00 pm Kentucky Theatre

Sevendust at Manchester Music Hall

 Tue, 21 Apr at 06:50 pm Manchester Music Hall

Monster Jam

 Sun, 21 Jun at 02:00 pm Rupp Arena

Bernadette Peters

 Sat, 09 May at 07:00 pm Lexington Opera House

Nitro Circus

 Sat, 29 Aug at 07:00 pm Legends Field - KY

Atreyu in Lexington

 Tue, 21 Apr at 07:00 pm Manchester Music Hall

Magic for Adults: Lexington, KY

 Sun, 26 Jul at 07:30 pm Comedy Off Broadway

Lavell Crawford - May 22-24, 2026

 Fri, 22 May at 07:00 pm Comedy Off Broadway

Vinyl Richie @ Keeneland Derby Party!

 Sat, 02 May at 12:00 pm Keeneland

five below band at Central Bank Thursday Night Live

 Thu, 21 May at 05:30 pm Central Bank Thursday Night Live

Shovels and Rope

 Wed, 22 Apr at 07:00 pm The Burl

The Head and The Heart at CommonSpirit Health Stage at Gatton Park

 Thu, 23 Jul CommonSpirit Health Stage at Gatton Park

Bluey's Big Play

 Fri, 07 Aug at 07:00 pm Lexington Opera House USD 49 to 135

Brit Floyd

 Fri, 25 Sep at 07:00 pm CommonSpirit Health Stage at Gatton Park

Lavell Crawford

 Thu, 21 May Comedy Off Broadway

Lavell Crawford

 Fri, 22 May at 11:00 pm Comedy Off Broadway

Hayden Coffman in Lexington

 Sat, 09 May at 09:00 pm The Burl

Magic City Hippies in Lexington

 Thu, 06 Aug at 07:00 pm The Burl

Jessica Kirson at Comedy Off Broadway

 Fri, 29 May at 07:00 pm Comedy Off Broadway

Lexington Pride Bar Crawl

 Sat, 20 Jun at 04:00 pm Tapster Lexington, KY – Self Pour Bar & Tasting Room USD 0 to 31

Shakey Graves in Lexington

 Sat, 06 Jun at 05:00 pm The Red Mile

Greek Sing at Rupp Arena

 Sat, 25 Apr at 05:00 pm Rupp Arena

Little River Band in Lexington

 Sat, 13 Jun at 07:00 pm Gatton Park on the Town Branch

Last Podcast on The Left

 Sat, 25 Apr at 07:00 pm Manchester Music Hall

49 Winchester at The Burl

 Fri, 24 Apr The Burl

Flatland Cavalry in Lexington

 Sat, 25 Apr at 12:00 pm Gatton Park on the Town Branch

Shovels & Rope

 Fri, 24 Apr The Burl

Tahlsound Presents | A Celebration of Women Songwriters: Abby Hamilton, Girl Tones, Emily Jamerson

 Sun, 26 Apr at 05:00 pm 302 Southland Drive, Lexington, KY, United States, Kentucky

Josh Blue

 Wed, 17 Jun at 07:00 pm Comedy Off Broadway USD 77 to 96

Tahlsound Presents | The John Hartford Jamboree: Hancock & Shouse-The Tillers-JH Fiddle Tune Project

 Sun, 24 May at 05:00 pm 302 Southland Drive, Lexington, KY, United States, Kentucky

49 Winchester

 Thu, 23 Apr at 07:00 pm The Burl

Tigers Jaw in Lexington

 Fri, 29 May at 07:00 pm The Burl

Steve Hofstetter in Lexington, KY! (7:30 PM)

 Sat, 20 Jun at 07:30 pm Lyric Theatre & Cultural Arts Center USD 7 to 185

Memphis May Fire in Lexington

 Sun, 19 Jul at 07:00 pm Headliners Music Hall

Lexington Porch Fest

 Sat, 06 Jun at 12:00 pm Lexington, KY

Jeff Arcuri - April 23-25, 2026

 Thu, 23 Apr at 07:00 pm Comedy Off Broadway

Thee Sinseers & The Altons

 Wed, 29 Apr at 07:00 pm The Burl

Owen Riegling, Payton Smith in Lexington

 Sat, 03 Oct at 07:00 pm The Burl

WGE - Lexington Open XXVIII powered by Prodigy and Bomb Discs

 Fri, 15 May at 12:00 pm Jacobson Park, Lexington, KY 40509, United States

Bluey's Big Play at Lexington Opera House

 Sat, 08 Aug at 11:00 am Lexington Opera House

Braxton Keith in Lexington

 Sun, 07 Jun at 02:30 pm The Red Mile

Tommy James and the Shondells at CommonSpirit Health Stage at Gatton Park

 Sat, 18 Jul CommonSpirit Health Stage at Gatton Park

Whose Live Anyway at Lexington Opera House

 Tue, 19 May at 07:30 pm Lexington Opera House

Monster Jam

 Sat, 20 Jun at 02:00 pm Rupp Arena

Kenny Wayne Shepherd Band

 Thu, 08 Oct Lexington Opera House

A Killer Good Drag Show

 Sun, 14 Jun at 01:00 pm The Willow - a blooming collective

West Sixth Brewing & Smithtown Seafood: Derby Party Feast

 Sat, 02 May at 05:00 pm West Sixth Brewing USD 4 to 64

UK Symphony Orchestra - Brahms Requiem with UK Choirs and Lexington Singers at Singletary Center of Arts

 Fri, 24 Apr at 07:30 pm Singletary Center of Arts

Hugh Howser at Comedy Off Broadway

 Wed, 22 Apr at 07:00 pm Comedy Off Broadway

Leslie Jones: I'm Hot Tour

 Fri, 11 Sep at 08:00 pm Lexington Opera House

Zarna Garg

 Thu, 04 Jun at 07:00 pm Comedy Off Broadway

Amber Autry at Comedy Off Broadway

 Sat, 02 May at 06:30 pm Comedy Off Broadway

Giovannie and The Hired Guns

 Sat, 02 May at 07:00 pm Manchester Music Hall

Kentucky Punk Rock Flea Market

 Sat, 03 Oct at 12:00 pm Bluegrass Convention Center

Lexington Cinco De Mayo Bar Crawl

 Tue, 05 May at 05:00 pm Belle's Cocktail House USD 8 to 32

Open Barn & BBQ

Thu, 23 Apr at 04:30 pm 719 Dolan Lane, Lexington, KY, United States, Kentucky 40511

Shapel Lacey at Comedy Off Broadway

 Thu, 21 May Comedy Off Broadway

Lexington Renaissance Faire

 Sat, 22 Aug at 10:00 am Masterson Station Park

Greyline Social - Kickoff Party!

 Fri, 08 May at 05:00 pm Greyline Station, Lexington KY

Tigers Jaw

 Thu, 28 May at 07:00 pm The Burl

Invent Animate in Lexington

 Sun, 31 May at 06:00 pm Manchester Music Hall

Jim Henson's Fraggle Rock Live

 Wed, 30 Sep at 07:00 pm Lexington Opera House

Old North Drag Brunch

Sun, 26 Apr at 11:30 am Old North Bar

LexiCon Board Game & RPG Convention

 Fri, 15 May at 12:00 pm 1950 Newtown Pike, Lexington, KY, United States, Kentucky 40511

Comedy Show: Naim Ali Live at The Spot: Lex

 Sat, 02 May at 07:30 pm The Spot: Lex USD 13 to 18

Laci Kaye Booth in Lexington

 Sat, 06 Jun The Red Mile

Derrick Stroup

 Thu, 14 May at 07:00 pm Comedy Off Broadway

Dedrick Flynn - May 8-10, 2026

 Fri, 08 May at 07:00 pm Comedy Off Broadway

Brunch off Broadway a Musical Drag Brunch

 Sun, 17 May at 11:00 am 21c Museum Hotel Lexington USD 61

Dr. Suess's The Cat In The Hat at Lexington Opera House

 Wed, 22 Apr Lexington Opera House

2026 Feather the Nest - Variety Show & Fundraiser - Blackbox Theater Lexington, KY

 Sat, 02 May at 05:30 pm Pam Miller Downtown Arts Center

Fit For A King

 Sun, 31 May at 11:00 pm Manchester Music Hall

S.G. Goodman

 Thu, 14 May at 07:00 pm The Burl

Dedrick Flynn at Comedy Off Broadway

 Thu, 07 May at 07:00 pm Comedy Off Broadway

Kiddie Kapers and Company Dance Recital at Lexington Opera House

 Fri, 08 May Lexington Opera House

Dale Jones

 Wed, 24 Jun at 07:00 pm Comedy Off Broadway

Margarita Wars

 Tue, 05 May at 06:00 pm The Rackhouse Tavern USD 25

2026 A Dancer’s Journey Gala Show: Echoes of the East

 Sat, 30 May at 06:00 pm Pam Miller Downtown Arts Center

Kentucky Derby Hats and Heels Day Party

 Sat, 02 May at 05:00 pm 160 Moore Dr USD 29 to 375

Golden! A K-Pop Kids Party

 Sat, 06 Jun at 07:00 pm Manchester Music Hall

Drake Milligan

 Fri, 08 May at 12:00 am The Burl