Halloween Weekend in the Boograss

Sarah Gossett


Halloween CycleScream Costume Contest & Benefit

Date: Friday, October 27th 6:30pm – 9:00pm

Location: CycleBar (4049 Finn Way, Lexington, KY)

If you enjoy dressing up, getting fit and supporting a good cause, CycleBar has just the event for you! The studio will be hosting a 50-minute workout/costume contest with awards for Biggest Team, Best Team Costume and Best Individual Costume. After breaking a sweat, head over to Whole Foods Market Café for the post-ride happy hour to enjoy a free healthy drink and light apps. Winners of the contest will be given their prizes from Chew Brunch Series, West Sixth Brewery, Whole Foods Market and Cafe, Crave Lexington, Sorella Gelateria, and more! Reserve your bike for $40 at https://fritzfarm.cyclebar.com/class-detail/?apptid=3619970 and RSVP your attendance to the happy hour at [email protected]. 100% of the proceeds will benefit Take Steps Lexington to support the Crohn's & Colitis Foundation and fund research to find cures for IBDs! Patients are invited to the post-ride happy hour regardless of participation in the ride!

Safety City Trick or Treat Night

Date: Friday, October 27th 6:00pm - 8:00pm 

Location: Safety City (1160 Harry Sykes Way, Lexington, KY)

Want your children to learn how to be safe when Trick-or-Treating on Halloween? Bring the whole family to Safe City’s Trick or Treat Night! Organizations from the community will be handing out candy, along with resources and safety information for kids and families. The event is free for children up to age 12. 

Haunted Frontier  

Date: Friday, October 27th - 29th 7:00pm - 10:00pm 

Location: Fort Harrod State Park (100 S College Street, Harrodsburg, KY)

Experience a haunted house 243 year in the making! This gathering is not for the faint of heart. The haunt begins at the Old Fort Harrod and makes its way through the darkness and the fog to the oldest cemetery in all of Kentucky. Explore the haunted history of these historic grounds for only $7. Call (859) 734-3314 for tickets and more details. 

The Cemetery Crawl: History and Mystery of the Kentucky Horse Park 

Date: October 28th and 29th at 4:30pm, 5:30pm & 6:30pm

Location: Kentucky Horse Park (4089 Iron Works Parkway, Lexington, KY)

Explore the spooky history of the Kentucky Horse Park during this limited cemetery tour. Hop on one of the hayrides to join the crawl and listen to the chilling stories of the ghouls and ghosts that plague these historic grounds with hauntings. Tickets are $15 per person. Reservations can be made by calling (859) 259-4213. 

HalloWhinny Fall Festival

Date: Sunday, October 29th 1:00pm – 6:00pm

Location: Kentucky Horse Park (4089 Iron Works Parkway, Lexington, KY)

Roasting marshmallows, hay rides, pumpkins, crafts and more! Tis the season for all things Autumn, and the Kentucky Horse Park has made it easy to do all of your favorite fall activities in one afternoon! Get the whole family (even little Scruffy) dressed up and head to the HalloWhinny Fall Festival! There will be a costume contest for children AND pets! Also, the first 100 people will receive a special Halloween-themed gift! Don’t want to fill up on marshmallows for dinner? Don’t worry! Food trucks and craft beer will also be available!

Wicked Wonders Art Market

Date: Sunday, October 29th from 11:00 AM - 8:00 PM 

Location: Cheapside Park (251 W. Main St., Lexington, KY)

Join the Halloween festivities downtown at the Fifth Third Pavilion! The arts and crafts displayed at the Wicked Wonders Art Market will be frighteningly delightful. Be careful wandering off too far though; the undead are just around the corner! But fear not, there will be food trucks around to keep the zombies’ munchies at bay. 

Thriller and Halloween Parade

Date: Sunday, October 29th 2:00 PM - 10:00 PM 

Location: Corner of Main and Mill Street

The funk of forty-thousand years surfaced in Michael Jackson’s legendary video in 1983. Even to this day, zombies and the undead gather in the streets of downtown Lexington every year and recreate the terrifying dance craze to celebrate Halloween. They are always looking for more bodies, so become one of the undead and be part of this Lexington tradition by signing up at www.lexingtonky.gov. 

Earth Dog Spa presents Trick or Treat and Meet!

Date: Monday, October 30th 6:00pm - 8:00pm 

Location: Earth Dog Spa & Apawthecary (713 Allendale Drive, Lexington, KY)

Think that people with kids get to have all of the fun for Halloween? Think again! Even parents of “fur babies” can go trick or treating with their furry children this year. Break in yours and you pets’ costumes a day early and head over to Earth Dog Spa for the purrrfect trick or treating experience! Pup treat bags and Pupcakes by Baby Cakes will be offered for your fur babies, but don’t be afraid to bring the whole family! There will be cookies and punch provided, and even some candy to satisfy your little humans. Enter to win some scary good prizes, including free grooming services, products, and even a month supply of dog food from pet wants Lex! 

Trick or Treat at Blue Grass Stockyard 

Date: Tuesday, October 31st 5:00pm - 8:00pm 

Location: Blue Grass Stockyard (4561 Iron Works Pike, Lexington, KY)

Searching for last minute Halloween night plans for the family? Go see the amazing ponies and farm animals from Rosie’s Ponies and Petting Zoo AND snag some sweets at the new Blue Grass Regional Marketplace! Play games for prizes and snack on refreshments from Hayden's Stockyard Eatery.

Yonder Mountain String Band - Halloween Concert

Date: Tuesday, October 31st 8:00pm - 11:00pm 

Location: Manchester Music Hall (899 Manchester St., Lexington, KY)

Celebrate Halloween “Boo-grass” style with a performance by Yonder Mountain String Band at Manchester Music Hall with special guest, The Last Revel! The contemporary bluegrass band has recently released their first album in two years called “LOVE. AIN’T LOVE” as a tribute to their unique brand. Tickets for the concert are available at ticketfly.com, in-person at CD Central, or by phone at (877) 435-9849.