Lucky you. You just found LEXtoday’s Plan Ahead, a list of some of the biggest events to plan for that are taking place throughout the Horse Capital of the World each month.
Take out your calendar, grab your day planner, or text all your friends — these are the top events we recommend heading to this month. Psst: Don’t forget to bookmark this page and come back; we update our guide monthly.
(Don’t see anything you like? Check out our full events calendar.)
Music + comedy
Eric Church: Free The Machine Tour | Friday, Oct. 3 | 7:30 p.m. | Rupp Arena | $54+ | Sing along to your favorite country anthems, cheer with a beer in hand, and let Eric Church and Marcus King bring the house down.
Jammy Buffet | Sunday, Oct. 12 | 7 p.m. | The Burl | $10+ | Grab a margarita, throw on your Hawaiian shirt, and dance along to the ultimate Jimmy Buffett tribute night.
Adam Sandler: You’re My Best Friend Tour | Thursday, Oct. 16 | 7:30 p.m. | Rupp Arena | $49+ | Laugh until you cry as Adam Sandler delivers brand-new jokes, songs, and all the weirdness you love.
Seasonal
Keeneland Opening Day | Friday, Oct. 3 | 11 a.m.–5 p.m. | Keeneland Race Course | $10+ | Celebrate the start of the Fall Meet at Keeneland. Sip mimosas, stroll the historic grounds, admire stunning horses, and soak in the excitement of Opening Day at this iconic Lexington track.
Keeneland College Scholarship Day | Friday, Oct. 10 | 11 a.m.–3 p.m. | Keeneland Racecourse | Free | Full-time college students can attend Keeneland College Scholarship Day with free admission, reserved seating, and goodie bags often with T-shirts, mocktails, and food tickets.
The Ghost Walk of Lexington | Saturday, Oct. 25 | 8 p.m. | Carnegie Center for Literacy & Learning | $20 | Take the longest-running historical ghost walk in Lexington. Wander Gratz Park with guides and hear chilling tales of lingering spirits.
Halloween Festival + Thriller Parade | Sunday, Oct. 26 | 4:45–6 p.m. (variety show), 6:30–7 p.m. (parade), 7–9 p.m. (Thriller) | Downtown Lexington | Free | Catch spooky skits, watch zombies dance “Thriller” in the street, and join the city’s biggest Halloween bash.
Pumpkin Patch Classic | Saturday, Oct. 11 | 8:30 a.m. & 2 p.m. | Tates Creek Golf Course | $70+ | Tee off at this 18-hole scramble tournament celebrating fall. Morning and afternoon sessions available — register early to secure your spot.
PumpkinMania | Sunday, Oct. 26 | TBD | Old Morrison Circle, Transylvania University | Free | Participants can reserve their pumpkins beginning Oct. 1. Attendees will carve pumpkins as part of a community event and see their creations light the historic steps of Old Morrison.
For the fam
Freaky Flicks Movie Series: “Hocus Pocus” | Friday, Oct. 3 | 6:30 p.m. pre-show, movie at dark (~7:30 p.m.) | Masterson Station Park | Free | Kick off spooky season with Freaky Flicks. Dance, watch “Hocus Pocus,” join the kids’ costume contest, and enjoy food trucks or a picnic.
Jack-o-lantern Trail | Wednesday, Oct. 22–Saturday, Oct. 25 | 6–9 p.m. | Lexington trails | $6+ | Wander a glowing path lined with carved pumpkins and snap the perfect fall photo for your feed.
Lexington Trick-or-Treat | Friday, Oct. 31 | 6–8 p.m. | Citywide | Free | Put on your best costume, grab your candy bucket, and hit the streets for Lexington’s sweetest night of the year.
Get social
Poetry at the Table | Wednesday, Oct. 1 | 5:30 p.m. | Kenwick Table | Free | Join us on the first Wednesday of the month for an evening of poetry, including featured performers, an open mic, and the most supportive audience in Lexington.
Showgirl Era Album Listening Party | Friday, Oct. 3 | 6:30–9 p.m. | Ghost Fox Winery | $45+ | Step into the Showgirl Era. Enjoy a first listen to Taylor’s new album, charcuterie, themed cocktails, bracelet-making, and Swiftie fun.
Carve & Chip’n | Sunday, Oct. 19 | 1–5 p.m. | McConnell Springs Park | Free | Bring your own pumpkin and get creative at McConnell Springs. Carve, use stencils, enjoy food trucks, and see your pumpkin on the Jack-o’-lantern Trail.
Yappy Hour: Howl-o-ween Party | Wednesday, Oct. 29 | 5:30–7:30 p.m. | Jacobson Dog Park | Free | Bring your furry friend to a spook-tacular Howl-o-ween. Enter the pay-what-you-like costume contest, enjoy live music, food trucks, drinks, and pup-friendly fun.
Have an event of your own you want to share with us? Follow these easy steps to add your events to our calendar:
- Go to our Events page.
- Click “Add Event” in the top right-hand corner.
- Make sure to include a link and fill out important information like the date, time, location, and price of your event.
- Click “Submit,” and you’ve just added an event to our website calendar.