| Event | Venue | Date/Time | |
| 2026 SEC Softball Tournament - Session 5 | John Cropp Stadium
Lexington, KY | Thursday
5/7/2026
5:00 PM |  |
| Lexington Legends vs. Lancaster Stormers | Legends Field - KY
Lexington, KY | Thursday
5/7/2026
6:45 PM | |
| Drake Milligan | The Burl
Lexington, KY | Thursday
5/7/2026
8:00 PM | |
| 2026 SEC Softball Tournament - Session 6 | John Cropp Stadium
Lexington, KY | Friday
5/8/2026
4:00 PM | |
| Lexington Legends vs. Lancaster Stormers | Legends Field - KY
Lexington, KY | Friday
5/8/2026
7:00 PM | |
| Clayton English | Comedy Off Broadway
Lexington, KY | Friday
5/8/2026
7:00 PM | |
| Kiddie Kapers & Company Dance Recital | Lexington Opera House
Lexington, KY | Friday
5/8/2026
7:00 PM | |
| Lexington Sporting Club vs. Monterey Bay FC | Lexington SC Stadium
Lexington, KY | Friday
5/8/2026
7:30 PM | |
| 2026 SEC Softball Tournament - Championship Session | John Cropp Stadium
Lexington, KY | Saturday
5/9/2026
5:00 PM | |
| Lexington Legends vs. Lancaster Stormers | Legends Field - KY
Lexington, KY | Saturday
5/9/2026
7:00 PM | |
| Ingested | Manchester Music Hall
Lexington, KY | Saturday
5/9/2026
7:30 PM | |
| Lexington SC Women's Team vs. Brooklyn FC | Lexington SC Stadium
Lexington, KY | Sunday
5/10/2026
2:00 PM | |
| Lexington Legends vs. Lancaster Stormers | Legends Field - KY
Lexington, KY | Sunday
5/10/2026
2:00 PM | |
| Bernadette Peters | Lexington Opera House
Lexington, KY | Sunday
5/10/2026
7:30 PM | |
| New Found Glory | Manchester Music Hall
Lexington, KY | Monday
5/11/2026
7:30 PM | |
| Kentucky Wildcats vs. Northern Kentucky Norse | Kentucky Proud Park
Lexington, KY | Tuesday
5/12/2026
6:30 PM | |
| Local Arts Spotlight | Lexington Opera House
Lexington, KY | Wednesday
5/13/2026
7:30 PM | |
| Christone Kingfish Ingram | Manchester Music Hall
Lexington, KY | Wednesday
5/13/2026
8:00 PM | |
| Kentucky Wildcats vs. Arkansas Razorbacks | Kentucky Proud Park
Lexington, KY | Thursday
5/14/2026
6:30 PM | |
| Saving Abel | Manchester Music Hall
Lexington, KY | Thursday
5/14/2026
7:30 PM | |
| Kentucky Wildcats vs. Arkansas Razorbacks | Kentucky Proud Park
Lexington, KY | Friday
5/15/2026
6:30 PM | |
| S.G. Goodman | The Burl
Lexington, KY | Friday
5/15/2026
7:00 PM | |
| Demon Hunter | Manchester Music Hall
Lexington, KY | Friday
5/15/2026
7:30 PM | |
| Lexington Philharmonic & Lexington Singers: Symphony of Sound | Lexington Opera House
Lexington, KY | Friday
5/15/2026
7:30 PM | |
| Kentucky Wildcats vs. Arkansas Razorbacks | Kentucky Proud Park
Lexington, KY | Saturday
5/16/2026
2:00 PM | |
| Phil Wickham | Rupp Arena At Central Bank Center
Lexington, KY | Saturday
5/16/2026
7:00 PM | |
| Molly Tuttle & Maggie Rose | The Burl
Lexington, KY | Saturday
5/16/2026
8:00 PM | |
| Buckcherry | Manchester Music Hall
Lexington, KY | Saturday
5/16/2026
8:00 PM | |
| Lexington Legends vs. Southern Maryland Blue Crabs | Legends Field - KY
Lexington, KY | Tuesday
5/19/2026
6:45 PM | |
| Whose Live Anyway? | Lexington Opera House
Lexington, KY | Tuesday
5/19/2026
7:30 PM | |
| Lexington Legends vs. Southern Maryland Blue Crabs | Legends Field - KY
Lexington, KY | Wednesday
5/20/2026
10:30 AM | |
| Lexington Legends vs. Southern Maryland Blue Crabs | Legends Field - KY
Lexington, KY | Thursday
5/21/2026
6:45 PM | |
| Shapel Lacey | Comedy Off Broadway
Lexington, KY | Thursday
5/21/2026
7:00 PM | |
| Ken Ludwig's The Gods of Comedy | Carriage House Theatre - Lexington
Lexington, KY | Thursday
5/21/2026
7:30 PM | |
| Ethan Regan | The Burl
Lexington, KY | Thursday
5/21/2026
8:00 PM | |
| The Sixties Show | Lexington Opera House
Lexington, KY | Thursday
5/21/2026
8:00 PM | |
| Lexington Legends vs. Southern Maryland Blue Crabs | Legends Field - KY
Lexington, KY | Friday
5/22/2026
7:00 PM | |
| Lavell Crawford | Comedy Off Broadway
Lexington, KY | Friday
5/22/2026
7:00 PM | |
| WWE: Smackdown | Rupp Arena At Central Bank Center
Lexington, KY | Friday
5/22/2026
7:30 PM | |
| Ken Ludwig's The Gods of Comedy | Carriage House Theatre - Lexington
Lexington, KY | Friday
5/22/2026
7:30 PM | |
| Lavell Crawford | Comedy Off Broadway
Lexington, KY | Friday
5/22/2026
9:30 PM | |
| Lavell Crawford | Comedy Off Broadway
Lexington, KY | Saturday
5/23/2026
6:30 PM | |
| Lexington Legends vs. Southern Maryland Blue Crabs | Legends Field - KY
Lexington, KY | Saturday
5/23/2026
7:00 PM | |
| Ken Ludwig's The Gods of Comedy | Carriage House Theatre - Lexington
Lexington, KY | Saturday
5/23/2026
7:30 PM | |
| Lavell Crawford | Comedy Off Broadway
Lexington, KY | Saturday
5/23/2026
9:00 PM | |
| Lexington Legends vs. Southern Maryland Blue Crabs | Legends Field - KY
Lexington, KY | Sunday
5/24/2026
2:00 PM | |
| Ken Ludwig's The Gods of Comedy | Carriage House Theatre - Lexington
Lexington, KY | Sunday
5/24/2026
2:30 PM | |
| Lavell Crawford | Comedy Off Broadway
Lexington, KY | Sunday
5/24/2026
7:00 PM | |
| Lexington Legends vs. Gastonia Ghost Peppers | Legends Field - KY
Lexington, KY | Tuesday
5/26/2026
6:45 PM | |
| Lexington Legends vs. Gastonia Ghost Peppers | Legends Field - KY
Lexington, KY | Wednesday
5/27/2026
10:30 AM | |
| Lexington Legends vs. Gastonia Ghost Peppers | Legends Field - KY
Lexington, KY | Thursday
5/28/2026
6:45 PM | |
| Mac McAnally | Lexington Opera House
Lexington, KY | Thursday
5/28/2026
8:00 PM | |
| The Mountain Goats | Manchester Music Hall
Lexington, KY | Thursday
5/28/2026
8:00 PM | |
| Lexington Legends vs. High Point Rockers | Legends Field - KY
Lexington, KY | Friday
5/29/2026
7:00 PM | |
| Jessica Kirson | Comedy Off Broadway
Lexington, KY | Friday
5/29/2026
7:00 PM | |
| Ken Ludwig's The Gods of Comedy | Carriage House Theatre - Lexington
Lexington, KY | Friday
5/29/2026
7:30 PM | |
| COLD | Manchester Music Hall
Lexington, KY | Friday
5/29/2026
8:00 PM | |
| Jessica Kirson | Comedy Off Broadway
Lexington, KY | Friday
5/29/2026
9:30 PM | |
| Jessica Kirson | Comedy Off Broadway
Lexington, KY | Saturday
5/30/2026
6:30 PM | |
| Lexington Legends vs. High Point Rockers | Legends Field - KY
Lexington, KY | Saturday
5/30/2026
7:00 PM | |
| Ken Ludwig's The Gods of Comedy | Carriage House Theatre - Lexington
Lexington, KY | Saturday
5/30/2026
7:30 PM | |
| Jessica Kirson | Comedy Off Broadway
Lexington, KY | Saturday
5/30/2026
9:00 PM | |
| Lexington Legends vs. High Point Rockers | Legends Field - KY
Lexington, KY | Sunday
5/31/2026
2:00 PM | |
| Ken Ludwig's The Gods of Comedy | Carriage House Theatre - Lexington
Lexington, KY | Sunday
5/31/2026
2:30 PM | |
| Fit For A King, Invent Animate, Ten56 & Acres | Manchester Music Hall
Lexington, KY | Sunday
5/31/2026
7:00 PM | |
| Tophouse | The Burl
Lexington, KY | Thursday
6/4/2026
8:00 PM | |
| Zarna Garg | Comedy Off Broadway
Lexington, KY | Friday
6/5/2026
7:00 PM | |
| Ken Ludwig's The Gods of Comedy | Carriage House Theatre - Lexington
Lexington, KY | Friday
6/5/2026
7:30 PM | |
| I've Got Friends - Garth Brooks Tribute Band | Manchester Music Hall
Lexington, KY | Friday
6/5/2026
8:00 PM | |
| Bayker Blankenship | The Burl
Lexington, KY | Friday
6/5/2026
8:00 PM | |
| Zarna Garg | Comedy Off Broadway
Lexington, KY | Friday
6/5/2026
9:30 PM | |
| Railbird Festival - 2 Day Pass | The Red Mile
Lexington, KY | Saturday
6/6/2026
TBD | |
| Railbird Festival: The Lumineers, Caamp & Mt. Joy (Time: TBD) - Saturday | The Red Mile
Lexington, KY | Saturday
6/6/2026
12:00 PM | |
| Zarna Garg | Comedy Off Broadway
Lexington, KY | Saturday
6/6/2026
6:30 PM | |
| Ken Ludwig's The Gods of Comedy | Carriage House Theatre - Lexington
Lexington, KY | Saturday
6/6/2026
7:30 PM | |
| Zarna Garg | Comedy Off Broadway
Lexington, KY | Saturday
6/6/2026
9:00 PM | |
| Golden! A K-Pop Kids Party | Manchester Music Hall
Lexington, KY | Sunday
6/7/2026
11:00 AM | |
| Railbird Festival: Tyler Childers, Zach Top & Ella Langley (Time: TBD) - Sunday | The Red Mile
Lexington, KY | Sunday
6/7/2026
12:00 PM | |
| Ken Ludwig's The Gods of Comedy | Carriage House Theatre - Lexington
Lexington, KY | Sunday
6/7/2026
2:30 PM | |
| Edwin McCain & Five for Fighting | Lexington Opera House
Lexington, KY | Sunday
6/7/2026
7:30 PM | |
| Lexington Legends vs. Gastonia Ghost Peppers | Legends Field - KY
Lexington, KY | Tuesday
6/9/2026
6:45 PM | |
| Lexington Legends vs. Gastonia Ghost Peppers | Legends Field - KY
Lexington, KY | Wednesday
6/10/2026
6:45 PM | |
| Lexington Legends vs. Gastonia Ghost Peppers | Legends Field - KY
Lexington, KY | Thursday
6/11/2026
6:45 PM | |
| Lexington Legends vs. Gastonia Ghost Peppers | Legends Field - KY
Lexington, KY | Friday
6/12/2026
7:00 PM | |
| UK Opera: Its A Grand Night for Singing | Concert Hall at Singletary Center for the Arts
Lexington, KY | Friday
6/12/2026
7:30 PM | |
| UK Opera: Its A Grand Night for Singing | Concert Hall at Singletary Center for the Arts
Lexington, KY | Saturday
6/13/2026
2:00 PM | |
| Lexington Legends vs. Gastonia Ghost Peppers | Legends Field - KY
Lexington, KY | Saturday
6/13/2026
7:00 PM | |
| Lexington Sporting Club vs. San Antonio FC | Lexington SC Stadium
Lexington, KY | Saturday
6/13/2026
7:00 PM | |
| Lexington Legends vs. Gastonia Ghost Peppers | Legends Field - KY
Lexington, KY | Sunday
6/14/2026
2:00 PM | |
| UK Opera: Its A Grand Night for Singing | Concert Hall at Singletary Center for the Arts
Lexington, KY | Sunday
6/14/2026
2:00 PM | |
| Steph Tolev | Comedy Off Broadway
Lexington, KY | Sunday
6/14/2026
7:30 PM | |
| Carly Pearce | Lexington Opera House
Lexington, KY | Tuesday
6/16/2026
7:30 PM | |
| Choir! Choir! Choir! | Manchester Music Hall
Lexington, KY | Tuesday
6/16/2026
8:00 PM | |
| Josh Blue | Comedy Off Broadway
Lexington, KY | Thursday
6/18/2026
7:00 PM | |
| Nick Shoulders | The Burl
Lexington, KY | Thursday
6/18/2026
8:00 PM | |
| Nearly Nicks | Manchester Music Hall
Lexington, KY | Thursday
6/18/2026
8:00 PM | |
| Josh Blue | Comedy Off Broadway
Lexington, KY | Friday
6/19/2026
6:30 PM | |
| Monty Python's Spamalot | Lexington Opera House
Lexington, KY | Friday
6/19/2026
7:30 PM | |
| UK Opera: Its A Grand Night for Singing | Concert Hall at Singletary Center for the Arts
Lexington, KY | Friday
6/19/2026
7:30 PM | |
| Monty Python's Spamalot | Lexington Opera House
Lexington, KY | Saturday
6/20/2026
1:00 PM | |
