2026 Breeders' Cup World Championship - Saturday Sat, 31 Oct at 08:30 am Keeneland Race Course SPORTS
Kenny Wayne Shepherd at Lexington Opera House Fri, 09 Oct at 08:00 pm Lexington Opera House TRIPS-ADVENTURES
PARKING: Kentucky Wildcats vs. LSU Tigers Fri, 09 Oct at 07:00 pm Kroger Field Parking Lots KENTUCKY-DERBY
Lexington Halloween Bar Crawl Sat, 24 Oct at 04:00 pm Tapster Lexington, KY – Self Pour Bar & Tasting Room USD 16 TO 46 FITNESS
FC Tulsa at Lexington SC at Lexington Sporting Club Stadium Fri, 09 Oct at 11:59 pm Lexington Sporting Club Stadium TRIPS-ADVENTURES
Manhattan Jaspers at Kentucky Wildcats Mens Basketball Tue, 03 Nov at 03:30 am Rupp Arena TRIPS-ADVENTURES
Lexington Murder Mystery 2: Crime on Date Night! Thu, 01 Oct at 12:00 am Phoenix Park USD 15 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
Bryant Bulldogs at Kentucky Wildcats Mens Basketball Tue, 08 Dec at 03:30 am Rupp Arena KENTUCKY-DERBY
Sacred Heart Pioneers at Kentucky Wildcats Mens Basketball Tue, 22 Dec at 03:30 am Rupp Arena TRIPS-ADVENTURES
Random Acts of Kindness Spree in Lexington, KY Thu, 08 Oct at 11:00 am Old School Coffee USD 27 TRIPS-ADVENTURES
Northern Arizona Lumberjacks at Kentucky Wildcats Mens Basketball Fri, 13 Nov at 03:30 am Rupp Arena KENTUCKY-DERBY
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
Evansville Purple Aces at Kentucky Wildcats Womens Basketball Wed, 11 Nov at 03:30 am Memorial Coliseum TRIPS-ADVENTURES
Charms & Chapters: Spooky Book Club | October 2026 Thu, 29 Oct at 07:00 pm doodles breakfast and lunch USD 25 TO 36 TRIPS-ADVENTURES
Homesteader Farm Tour Series | Bell Hollow Gardens Thu, 08 Oct at 09:00 am 820 Lane Allen Road, Suite 176, Lexington, KY 40504, Lexington, KY, United States, Kentucky 40504 TRIPS-ADVENTURES
ONE WAY 2 VEGAS SZN 7 LEXINGTON AUDITIONS #SITUATIONCHANGERS Sat, 17 Oct at 09:00 pm JUKEBOX BAR & LOUNGE USD 21 TO 87 FITNESS
The Commonwealth Cup! Sat, 10 Oct at 01:00 pm Waveland Museum Ln, Lexington, KY 40514, United States TRIPS-ADVENTURES
Foodies + New Friends: Lexington | All Ages Edition Wed, 17 Jun at 07:00 pm Restaurant of the Week USD 25 MEETUPS
Bike Night Finale Fri, 30 Oct at 05:30 pm 2073 Bryant Road, Lexington, KY, United States, Kentucky 40509 PARTIES
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
Halloween Experience— Watercolor Pumpkin Bouquet Paint Party Sat, 31 Oct at 11:00 am 2573 Richmond Road, Lexington, KY, United States, Kentucky 40509 ART
Bellarmine Knights at Kentucky Wildcats Womens Basketball Sun, 06 Dec at 03:30 am Memorial Coliseum TRIPS-ADVENTURES
The Nutcracker: Symphony of Lights Sat, 19 Dec at 07:00 pm Haggin Auditorium at Mitchell Fine Arts Center 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
2026 Kentucky Tree Climbing Championship Fri, 23 Oct at 08:00 am Woodland Park, Lexington, Kentucky SPORTS
Foodies + New Friends: Lexington | 20’s + 30’s Edition Sat, 13 Jun at 07:00 pm Restaurant of the Week USD 25 MEETUPS
Eastern Michigan Eagles at Kentucky Wildcats Womens Basketball Sun, 15 Nov at 03:30 am Memorial Coliseum KENTUCKY-DERBY
Ghosts of Lexington: Explore the Haunted Past! Sun, 01 Nov at 12:00 am 333 N Broadway, Lexington USD 8 TRIPS-ADVENTURES
Public Image Ltd at Manchester Music Hall Wed, 17 Mar at 08:00 pm Manchester Music Hall 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
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 Fri, 09 Jan at 07:00 pm Restaurant of the Week USD 105 TRIPS-ADVENTURES
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, 10 Oct at 04:00 pm 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