2026 Breeders' Cup World Championship - Saturday Sat, 31 Oct at 08:30 am Keeneland Race Course SPORTS
Manhattan Jaspers at Kentucky Wildcats Mens Basketball Tue, 03 Nov at 03:30 am Rupp Arena TRIPS-ADVENTURES
Salem MA "Halloween Red Eye Tour” | Oct 30th - Nov 1st, 2026 | $275 Per Person Fri, 30 Oct at 11:00 am Lexington, KY HALLOWEEN
Johnny Blue Skies & The Dark Clouds Thu, 29 Oct at 07:00 pm Rupp Arena At Central Bank Center TRIPS-ADVENTURES
Nutcracker! Magical Christmas Ballet - Lexington Sat, 07 Nov at 03:00 pm University of Kentucky TRIPS-ADVENTURES
Wichita State Shockers at Kentucky Wildcats Mens Basketball Fri, 27 Nov at 03:30 am Rupp Arena KENTUCKY-DERBY
Lexington Murder Mystery 2: Crime on Date Night! Thu, 01 Oct at 12:00 am Phoenix Park USD 15 TRIPS-ADVENTURES
Bryant Bulldogs at Kentucky Wildcats Mens Basketball Tue, 08 Dec at 03:30 am Rupp Arena KENTUCKY-DERBY
Evansville Purple Aces at Kentucky Wildcats Womens Basketball Wed, 11 Nov at 03:30 am Memorial Coliseum TRIPS-ADVENTURES
Sacred Heart Pioneers at Kentucky Wildcats Mens Basketball Tue, 22 Dec at 03:30 am Rupp Arena TRIPS-ADVENTURES
Gardner-Webb Runnin' Bulldogs at Kentucky Wildcats Mens Basketball Mon, 28 Dec at 03:30 am Rupp Arena KENTUCKY-DERBY
Marshall Thundering Herd at Kentucky Wildcats Womens Basketball Fri, 20 Nov at 03:30 am Memorial Coliseum KENTUCKY-DERBY
Haunted and Unhinged: A Walking History Tour Fri, 18 Sep at 08:00 pm Old Fayette County Court House USD 25 FITNESS
Northern Arizona Lumberjacks at Kentucky Wildcats Mens Basketball Fri, 13 Nov at 03:30 am Rupp Arena KENTUCKY-DERBY
Random Acts of Kindness Spree in Lexington, KY Wed, 28 Oct at 11:00 am Old School Coffee USD 27 TRIPS-ADVENTURES
Foodies + New Friends: Lexington | 20’s + 30’s Edition Sat, 13 Jun Restaurant of the Week USD 25 MEETUPS
Halloween Experience— Watercolor Pumpkin Bouquet Paint Party Sat, 31 Oct at 11:00 am 2573 Richmond Road, Lexington, KY, United States, Kentucky 40509 ART
Lexington, KY Murder Mystery: Solve the case! Sun, 01 Nov at 12:00 am 241 W Main St, Lexington, KY 40507 USD 10 TRIPS-ADVENTURES
Lexington’s Secret Society: An Outdoor Detective Game Sun, 01 Nov at 12:00 am 241 W Main St, Lexington, KY 40507 USD 10 CONTESTS
Bellarmine Knights at Kentucky Wildcats Womens Basketball Sun, 06 Dec at 03:30 am Memorial Coliseum TRIPS-ADVENTURES
Mister E of Imagination: Tales of Edgar Allan Poe Sat, 31 Oct at 02:00 pm Lexington Children's Theatre ART
The Nutcracker: Symphony of Lights Sat, 19 Dec at 07:00 pm Haggin Auditorium at Mitchell Fine Arts Center ART
🏍️ Extending Your Riding Season Workshop Sat, 07 Nov at 10:30 am 2073 Bryant Road, Lexington, KY, United States, Kentucky 40509 TRIPS-ADVENTURES
Pack the Bluegrass (Formerly Generosity Feeds Lexington) Sat, 07 Nov at 10:00 am 865 Greendale Rd, Lexington, KY, United States, Kentucky 40511 TRIPS-ADVENTURES
Single Awareness Dinner: Lexington | Foodies + New Friends Wed, 27 May at 07:00 pm Restaurant of the Week USD 24 TO 57 FITNESS
Eastern Michigan Eagles at Kentucky Wildcats Womens Basketball Sun, 15 Nov at 03:30 am Memorial Coliseum KENTUCKY-DERBY
Foodies + New Friends: Lexington | All Ages Edition Wed, 17 Jun Restaurant of the Week USD 25 MEETUPS
Ghosts of Lexington: Explore the Haunted Past! Sun, 01 Nov at 12:00 am 333 N Broadway, Lexington USD 8 TRIPS-ADVENTURES
Lexington Social Club Monthly: Foodies + New Friends Thu, 26 Nov Restaurant of the Month USD 13 MEETUPS
Sun-date Night/BFF Paint Party + 25% OFF DIY Candles! Sun, 08 Nov at 05:00 pm Painting with a Twist (Lexington, KY) DRAWING-PAINTING
Bike Night Finale Fri, 30 Oct at 05:30 pm 2073 Bryant Road, Lexington, KY, United States, Kentucky 40509 PARTIES
Weekday Deal Paint Party: Victorian Gothic Starting at $36 + $15 DIY Candles! Wed, 28 Oct at 06:30 pm Painting with a Twist (Lexington, KY) PARTIES
Public Image Ltd at Manchester Music Hall Wed, 17 Mar at 08:00 pm Manchester Music Hall TRIPS-ADVENTURES
Fantasy Book Club Paint Your Plot Workshop! Sun, 15 Nov at 05:00 pm Painting with a Twist (Lexington, KY) WORKSHOPS
Weekday Deal Paint Party: Starting at $36 + $15 DIY Candles! Wed, 21 Oct Painting with a Twist (Lexington, KY) PARTIES
NYC "Christmas in NYC" Red Eye Tour | Dec 11th -13th, 2026 $250 Per Person Fri, 11 Dec at 12:00 pm Lexington, KY
The Comeunity Project: Lexington | 30's Edition 2026 Mon, 26 Oct Restaurant of the Week USD 105 FITNESS
2026 Lexington Sporting Club Group Deposits Thu, 31 Dec at 03:30 am Lexington Sporting Club Stadium TRIPS-ADVENTURES
Drag Queen Sip and Paint Lexington The Drag Queen Paint experience Sat, 22 Aug 267 W Main St USD 47 TO 1,359 FITNESS
NYC Ball Drop New Year Eve Dec 30th, 2026 - Jan 1st, 2027 $250 Per Person Wed, 30 Dec at 12:00 pm Lexington, KY NEW-YEAR
Kent State Golden Flashes at Kentucky Wildcats Womens Basketball Mon, 28 Dec at 03:30 am Memorial Coliseum KENTUCKY-DERBY
Vanderbilt Commodores at Kentucky Wildcats Mens Basketball Sat, 16 Jan at 03:30 am Rupp Arena KENTUCKY-DERBY
Texas Longhorns at Kentucky Wildcats Womens Basketball Sun, 10 Jan at 03:30 am Memorial Coliseum KENTUCKY-DERBY
Louisville Cardinals at Kentucky Wildcats Womens Basketball Wed, 09 Dec at 03:30 am Rupp Arena TRIPS-ADVENTURES