Fall Fun in Kentucky


Fall Fun in Kentucky

Enjoy all of the wonderful ways to celebrate the season with Fall fun in Kentucky in the month of October 2023!

Know of more events? DM @BluegrassBlog on Instagram with details!


Image from LexingtonKY.gov

Skeleton Scavenger Hunt: 

Time/Date: Throughout October

Location: Downtown Cynthiana, KY 

Description: Search downtown for skeletons! 

Georgetown Autumnfest

Time/Date: Throughout October

Location: BiWater Farm in Georgetown, KY

Description: Fall in Love with Acres and Acres of Wide Open Family Fun! We Are Kentucky’s Largest Fall Farm Festival and it all starts in September.

You Pick Apples & Pumpkins

Time/Date: Through October 29th

Location: Eckerts Orchard in Versailles, KY

Description: Family friendly apple & pumpkin picking plus petting zoo, kids play area…

Harvest Festival

Time/Date: Throughout October Tuesday- Saturday

Location: Evans Orchard in Georgetown, KY

Description: Family friendly, kids area, fun, food & pumpkins


Harvest Market

Time/Date: Sept 30 & Oct 1st

Location: Wildside Winery in Versailles, KY

Description: Live music & local artists/makers

Legend of Sleepy Hollow

Location: Woodford Theatre in Versailles, KY

Time/Date: Through October 8th

Description: The spooky classic story by Washington Irving, presented with all the thrills, chills and laughs that keep young audiences on the edge of their seats. The storybook tale revolves around the main characters—the bumbling schoolteacher Ichabod, the coquettish Katrina and Ichabod’s brutish rival, Brom Bones.


Date: October 1st 10:00AM-5:00PM

Location: Eckert’s Orchard, Versailles, KY

Description: Wagon rides, live entertainment, great festival foods, children’s activities, and much more make this an apple pickin’ good time for everyone! There’s so much Fall fun in Kentucky!

Freaky Flicks 

Time/Date: October 6th, 13th, 20th. Pre-show activities start at 6:30 and the movie begins at dark. 

Location: Masterson Station Park for the first date and Moondance Amphitheater for the last two dates.  

Description: This year they will be showing Hocus Pocus, Casper, and Monsters Inc. There will be food and dessert trucks, as well as children’s activities prior to the movie! 


Opening Weekend of Ghost Walks: 

Time/Date: October 7th & 8th 

Location: Rohl’s Opera House

Description: An hour long walk through the streets of Cynthiana learning the stories of haunted buildings, murders, streets, and unexplained happenings. 

Pumpkin Jamboree 

Time/Date: Fridays and Saturdays in beginning October 7th 

Location: Eckert’s Orchard, Versailles, KY 

Description: fair food, live entertainment, children’s activities  

Pumpkin Focaccia Art Class:  

Time/Date: Sunday, October 8th

Location: Harkness Edwards Vineyards, Winchester,KY, 2:30-4:00PM 

Description: An afternoon of learning Focaccia bread art and wine! Make an edible piece of art.  

Halloween Lights Drive Thru: 

Time/Date: October 13th – 28th

Location: Ft. Boonesborough State Park, Richmond, KY 

Description: Enjoy the sights, sounds, and scares. Over one and a half miles of lights displays! 

Game of Homes

Time/Date: October 14th at 7PM

Location: The Depot on Main in Corbin, KY 

Description: Dinner theater event

Walking Dead Pub Crawl: 

Time/Date: October 21st 

Location: Downtown Cynthiana, KY  Gather the family for Fall fun in Kentucky!


Halloween Cupcake Class: 

Time/Date: Sunday, October 22, 12:00-1:30PM 

Location: Harkness Edwards Vineyards, Winchester,KY 

Description: Step by step instructions on how to create beautiful cupcakes! 

Hocus Pocus Charcuterie Class:  

Time/Date: Sunday, October 22, 2:30-4:00PM 

Location: Harkness Edwards Vineyards, Winchester,KY 

Description: Learn how to assemble your own charcuterie board 


October Makers Market

Time/Date: October 22nd 2-6PM

Location: Rock House Brewing in Lexington, KY

Description: Fall Makers Market


Jack-O-Lantern Trail 

Time/Date: Wednesday, Oct. 25 | Thursday, Oct. 26 | Friday, Oct. 27 | Saturday, Oct. 28 | Sunday Oct. 29 

Location: McConnell Springs Park 

Description: Campfires, smores, live owls, and hundreds of hand carved pumpkins lighting up the night!

Giant Pumpkin Contest Weigh In:  

Time/Date: October 27th 

Location: Courthouse, Cynthiana, KY 

Description: See who can grow the largest pumpkin! 

Thriller Parade

Time/Date: October 27th 

Location: Downtown Versailles, KY 

Description: Students from Jane’s School of Dance perform Thriller


Black Cat Chase 5K: 

Time/Date: October 27, 7:00-9:00PM 

Location: Downtown Frankfort, KY 

Description: Halloween costumes and music  

Full Moon Hike 

Time/Date: October 28th, 6:30-8:00pm 

Location: Raven Run Nature Sanctuary  

Description: Take a walk through the park at night and listen to all the nocturnal creatures while watching the moon rise! 

Boo on Main  

Time/Date: October 28th, 6:00AM-8:00PM 

Location: Downtown London, KY 

Description: Businesses and organizations line the streets to pass out candy and treats! 

Halloween and Thriller Parade:  

Time/Date: Sunday, October 29th 

Location: Downtown Lexington, KY 

Description: Halloween inspired art, live music, and a thriller parade. See link to participate.

Trick or Treating + Costume Parade 

Time/Date: October 29th, 2-4pm 

Location: Eckert’s Orchard, Versailles, KY 

Description: Come dressed in your costume to participate in the costume parade and be a part of the Fall fun in Kentucky

Enjoy all of the wonderful ways to celebrate the season with Fall fun in Kentucky in the month of October 2023!