LEXtoday City Guide Play Banner

Fall events happening in and around Lexington

Check out fall and Halloween-themed events happening in and around Lexington in this seasonal guide.


There’s demons closing in on every side. | Photo by Amy Wallot

Table of Contents

Ready for sweater weather, Lexington? From pumpkin patches and corn mazes to apple picking and German beer celebrations, fall is where the Horse Capital of the World thrives.

Get ready to come alive — or play dead at a fall-tastic favorite like the Thriller Parade — with this guide featuring 25 fall events happening between now and November.

Only in Lexington

Keeneland Fall Meet | Friday, Oct. 6-Saturday, Oct. 28 | Times vary | Keeneland, 4201 Versailles Rd. | $7-$150 | It’s not October in Lexington without a trip to our historic racetrack for horses, bourbon, and some bets.

“Thriller” Parade | Sunday, Oct. 29 | 7-9 p.m. | Main Street | Free | Night creatures will crawl through downtown when the annual “Thriller” reenactment brings hundreds of dancing zombies back to life.

Sip and savor

Fall Cocktail Class | Friday, Oct. 6 | 7 p.m. | The Kentucky Castle, 230 Pisgah Pike, Versailles | $74.76 | Stir + shake up three craft cocktails from the seasonal menu in this hands-on mixology experience.

Sippin’ With Griffin | Thursday, Oct. 19 | 6 p.m. | Griffin Gate Marriott Golf Resort & Spa, 1800 Newtown Pike | $20 | This bourbon flight experience will pair small bites with pours of Nelson’s Green Brier Distilling bourbons + walk you through the brand’s history and mash bill.

Cocktails with Zombies | Saturday, Oct. 21 | 7-10 p.m. | Lexington Children’s Theatre, 418 W. Short St. | $50 | See a special production of “Zombie in Love,” then mix, sip + mingle with fellow monsters featuring live jazz, spooky surprises, and tarot card readings.

Afternoon Tea | Sunday, Oct. 15 | 11 a.m. | The Kentucky Castle, 230 Pisgah Pike, Versailles | $97.76 | Treat yourself like royalty with an elegant tea party in the grand ballroom featuring sweet + savory bites.


Gather your ghouls + goblins for Freaky Friday Flicks at the park. | Photo by Paul Hooper

For the fam

Freaky Friday Flicks | Fridays, Oct. 6 | 6:30 p.m. | Masterson Station Park, 3051 Leestown Rd. | Free | Families are invited to bring your own picnic setup, check out local food and drink vendors, then kick back + relax for a showing of “Hocus Pocus.”

Freaky Friday Flicks | Friday Oct. 13 + Friday, Oct. 20. | 6:30 p.m. | Moondance Amphitheater, 1152 Monarch St. | Free | Families are invited to bring your own picnic setup, check out local food and drink vendors, then enjoy showings of “Casper” and “Monsters, Inc.” respectively.

Jack-o-lantern Trail | Wednesday, Oct. 25-Sunday, Oct. 29 | 6:30-10 p.m. | McConnell Springs Park, 416 Rebmann Ln. | $0-6 | This perfect fall evening will have you and your family marveling at the glow of hundreds of pumpkins, plus seasonal treats like s’mores, campfires, and visitors from Critters in the Classroom.

Halloween pumpkins lit up

Pick up your pals for a pumpkin stroll at McConnell Springs Park. | Photo by LEXtoday

Halloween happenings

Scarefest Weekend | Friday, Oct. 20-Sunday, Oct. 22 | Times vary | Central Bank Center, 430 W. Vine St. | $35.80-$148.79 | Meet your favorite scary movie celebs plus browse hundreds of vendors, entertainment, costume contests + more.

Hocus Pocus Brunch | Sunday, Oct. 22 | 10 a.m. + 2 p.m. | The Kentucky Castle, 230 Pisgah Pike, Versailles | $80.51 | The Sanderson sisters invite you to specialty-themed farm-to-table brunch with bubbles, sweets, and more — costumes encouraged.

A Cult Classic Halloween | Saturday, Oct. 28 | 8 p.m. | The Burl, 375 Thompson Rd. | $21.60 | Dress as your favorite cult classic movie character and groove to the sounds of Talking Heads cover band, Same As It Ever Was.

The Rocky Horror Picture Show | Saturday, Oct. 28 | 8:30 + 11:59 p.m. | Kentucky Theatre, 214 E. Main St. | $7.32 | See this cult classic and be mindful — some surprise cast members might be sitting right next to you.

PumpkinMania Festival | Sunday, Oct. 29 | 11 a.m.-4 p.m. | Transylvania University, 300 N. Broadway | Free | Head downtown for this family-friendly day to carve your pumpkin for this annual Halloween tradition. The pumpkins will then be on display through Thursday, Nov. 2.

Halloween Festival | Sunday, Oct. 29 | 5-7 p.m. | Robert F. Stephens Courthouse Plaza + Main Street | Free | Things kick off with the Halloween Variety Show, which includes spooky tunes and performances from area dance groups + bands, followed by the Halloween Parade.

Day of the Dead Celebration | Wednesday, Nov. 1 | 5-9 p.m. | Living Arts & Science Center, 362 N. Martin Luther King Blvd. | Free | Get creative and participate in art projects while seeing traditional performances, community-created Ofrendas, then follow the procession to the Old Episcopal Burying Grounds.

Spirit Strolls | Fridays + Saturdays, through Oct. 28 | 5:30 and 7:30 p.m. | Shaker Village, 501 Lexington Rd., Harrodsburg | $10-$15 | This guided walk will take you through the property while hearing spine-chilling journal entries of village dwellers’ past.

Just October fun

Good Foods Fall Fest | Saturday, Oct. 7 | 4-7 p.m. | Good Foods Co-op, 455 Southland Dr. | TKTK | Stop by for a full evening of live music, kids activities, local vendors, good food + good times.

The Drunken Flea | Sunday, Oct. 15 | 12-8 p.m. | The Burl, 375 Thompson Rd. | $3 | Wearhouse’s bi-annual curated vintage pop-up market will host dozens of vendors for all of your thrifting needs.

Spooky Printmaking | Wednesday, Oct. 18 | 7-9 p.m. | Rock House Brewing, 119 Luigart Ct. | $30 | Silver Solstice Prints will teach you basics of linocut printmaking so you can make + take home your own spooky print.

Distillery District Art & Music Festival | Friday, Oct. 20-Sunday, Oct. 22 | Distillery District, 1170 Manchester St. | Free | Stop by for food and drinks along with live music and art vendors from regional artists.

Silent Disco Dance Party | Thursday, Oct. 26 | 7-10 p.m. | The Grove, 200 W. Main St. | $20 | This fundraiser for LexArts will have you dancing to the beat of your own headset, because disco is not dead…it’s just silent.

Full Moon Hike | Saturday, Oct. 28 | 6:30-8 p.m. | Raven Run Nature Sanctuary, 3885 Raven Run Way | $5 | Take a guided walk through the park at night to look + listen for nocturnal wildlife as the moon rises.

Check out our other Guides
Check out these brunch restaurants, cafes, and diners in Lexington, serving a variety of egg dishes, mimosas, bloody marys, and more.
These 10 hiking trails cater to all skill levels in and around town.
Make the most of the warm weather with this list of the best local summer events and activities.
If you don’t have coffee already in hand, consider this your sign to grab some.
We’re highlighting the 21 best parks that Lexington, KY has to offer — complete with splash pads, playgrounds, walking trails, and even a few dog-friendly spots.
As Lexington continues to grow, we’re keeping an eye on upcoming developments and recently opened businesses.
We’re highlighting the best kid-friendly activities that Lexington, KY has to offer — complete with art classes, animal encounters, and outdoor fun.
From brands to artists, Lexington’s business scene is truly inspired.
To help make your entire process at Blue Grass Airport as smooth as possible, we’ve created a guide that covers everything from parking to details on the airport’s 16 nonstop flights.
Explore the Horse Capital of the World through its history, food, drink, and art on these tours.
LEXtoday phone
Good news for Lexington.
Get the best local news & events sent to your inbox each morning, for free.