Pumpkins & Thriller: 26 best things to do in and around Lexington this weekend

Matt Wickstrom
·7 min read

Here is a Lexington list and guide of the best weekend events around Central Kentucky on Friday, Saturday and Sunday if you are bored and need things to do including live music concerts, festivals and celebrations, food festivals, fall festivals, farmers markets, horse racing, comedy shows, opera performances, University of Kentucky sports like volleyball and soccer, kid-friendly and free events and craft fairs.

Jack-o-Lantern Trail at McConnell Springs Park

Traverse a lit pumpkin trail, enjoy s’mores and get up close with live owls from Critters in the Classroom at McConnell Springs Park on Oct. 27 from 6:30-10 p.m. $6. 416 Rebmann Ln. LexingtonKy.gov.

Comedian James Gregory at Comedy Off Broadway

Comedian James Gregory will make his return to Comedy Off Broadway on Oct. 27 and 28 at 6 and 8:30 p.m. $35. 161 Lexington Green Cir #C4. ComedyOffBroadway.com.

UK Men’s Soccer vs. West Virginia at The Bell

The UK Men’s Soccer team will face off against the West Virginia Mountaineers at the Bell Soccer Complex on Oct. 27 at 7 p.m. $5-8. 556 Wildcat Ct. UKathletics.com.

UK Men’s Basketball vs. Georgetown College at Rupp Arena

The UK Men’s Basketball team will take the court for its first exhibition game of the season against Georgetown College at Rupp Arena on Oct. 27 at 7 p.m. From $15. 430 W Vine St. UKathletics.com.

Lexington restaurant inspections lead to tossed hot dogs, chicken & more. See the list.

Black Cat Chase 5K in Downtown Frankfort

The Black Cat Chase 5K benefiting the YMCA of Central Kentucky will take place at the Old Capitol Lawn in downtown Frankfort on Oct. 27 at 7 p.m. $40. 300 W Broadway, Frankfort. RunSignUp.com.

SCAPA Presents “Finding Nemo Jr.” at the Lexington Opera House

Fayette County Public Schools’ School for The Creative and Performing Arts (SCAPA) will perform “Finding Nemo Jr.” at the Lexington Opera House on Oct. 27 at 7 p.m. and Oct. 28 at 2 and 7 p.m. From $17. 401 W Short St. LexingtonOperaHouse.com.

Horses enter the track during opening day of the Keeneland Fall Meet in Lexington, Ky., on Friday, Oct. 6, 2023.
Horses enter the track during opening day of the Keeneland Fall Meet in Lexington, Ky., on Friday, Oct. 6, 2023.

Keeneland Fall Meet’s last weekend of racing

Keeneland fall meet continues through Oct. 28 with the first call to post at 1 p.m. Gates will open at 11 a.m. Tickets (even general admission) must be purchased in advance online at tickets.Keeneland/racing or on the Keeneland Race Day App. General admission is $10 on Friday, Saturday and Sunday. You don’t need to buy tickets for the free tailgating area, The Hill, which is open Friday and Saturday. It has a betting tent, jumbo TV, live music and food trucks. No tickets are needed for Sunrise Trackside is 8 a.m. Oct. 28, with children’s activities, coffee and breakfast items at concession stand. 4201 Versailles Rd. Keeneland.com.

BOO-CHATA & BREWS at Rock House Brewing

Take part in bachata dancing, a costume contest and more during the second annual “Boo-Chata & Brews” event at Rock House Brewing on Oct. 27 from 8-11 p.m. Free. 119 Luigart Ct. Facebook.com.

The Taylor Party at Manchester Music Hall

Join fellow Swifties at Manchester Music Hall when The Taylor Party returns on Oct. 27 at 9 p.m. $15-30. l899 Manchester St. ManchesterMusicHall.com.

Lexington Cemetery Bird Walk

Join Central Kentucky Audubon Society for a morning birding walk at Lexington Cemetery, 833 W. Main St. Meet/park around the Henry Clay monument. 8:30-11:30 a.m. Free.

Day of the Dead at the Lexington Public Library

Join Casa De La Cultura for a special Día de los Muertos performance at the Lexington Public Library’s Village Branch on Oct. 28 from 12-1 p.m. Free. 1801 Alexandria Dr #136. LexPubLib.org. (Living Arts & Science Center, 362 N Martin Luther King Blvd., will have its traditional Day of the Dead Celebration 5-9 p.m. Nov. 1. with food trucks, performers, ofrendas and art projects.)

Claudia and Cecilia Garces wore a traditional face paint and headdress at the Festival del Dia de los Muertos at Living Arts and Science Center in Lexington, Ky., Sunday, November 1, 2015. Photo by Matt Goins
Claudia and Cecilia Garces wore a traditional face paint and headdress at the Festival del Dia de los Muertos at Living Arts and Science Center in Lexington, Ky., Sunday, November 1, 2015. Photo by Matt Goins

Hocus Pocus Cookie Decorating Class at Harkness Edwards Vineyards

Learn the basics of the royal icing technique during a “Hocus Pocus” themed cookie decorating and wine class at Harkness Edwards Vineyards on Oct. 28 at 1 p.m. $47. 5199 Combs Ferry Rd, Winchester. Facebook.com.

Spooky Sprint 5K at Coldstream Dog Park

The inaugural Spooky Sprint 5K benefiting the Lexington Humane Society at Coldstream Research Park will take place on Oct. 28 at 5 p.m. $20-35. 1850 Pisacano Dr. RunSignUp.com.

Weekend farmers markets

Even though the weather is cooler, the local farmers markets are still going strong. Bluegrass Farmers Market, 9 a.m. to 2 p.m. Oct. 28 at 1837 Plaudit Place, has seasonal produce, apples, eggs, baked goods and more for sale. Lexington Farmers Market, 8 a.m. to 2 p.m. Oct. 28 at Tandy Centennial Park on Main Street, and 10 a.m. to 2 p.m. Oct. 29 on Southland Drive, has seasonal produce, including pumpkins, gourds, mums, cheese, hot sauce and flowers for sale. Free. bluegrassfarmersmarket.com, lexingtonfarmersmarket.com

Boots & Bourbon Songwriter Festival at The Barn at McCall Springs

Listen to music from Nashville songwriters Lee Thomas Miller, Deric Ruttan, the Warren Brothers and Paul Carroll Binkley, take part in bourbon tastings and more during the Boots & Bourbon Songwriter Festival at The Barn at McCall Springs in Lawrenceburg on Oct. 28 from 6-11 p.m. $75-125. 2160 Harrodsburg Rd, Lawrenceburg. Eventbrite.com.

Halloween Bash at Wildside Winery

Wildside Winery in Versailles will host a spooktacular night of music, dancing, and more when its Halloween Bash returns on Oct. 28 from 6-9 p.m. 5500 Troy Pike, Versailles. Facebook.com.

UK Football vs. Tennessee at Kroger Field

UK Football will aim to get back in the win column when it welcomes the Tennessee Volunteers to Kroger Field on Oct. 28 at 7 p.m. From $125. 1540 University Dr. UKathletics.com.

Comedian Darren Knight at the Lexington Opera House

Comedian Darren Knight, better known as Southern Momma, will bring his Southern Momma & Friends Comedy Tour with Red Squirrel and Gary Cargal to the Lexington Opera House on Oct. 29 at 7 p.m. From $25. 401 W Short St. LexingtonOperaHouse.com.

Talking Heads Tribute Concert at The Burl

Dress as your favorite cult classic Halloween character as you get down to the music of the Talking Heads during a concert at The Burl on Oct. 28 at 8 p.m. $18. 375 Thompson Rd. TheBurlKy.com.

The Steel Woods Concert at Manchester Music Hall

Southern rock collective The Steel Woods will perform at Manchester Music Hall with support from Zach Top on Oct. 28 at 8 p.m. $25. 899 Manchester St. ManchesterMusicHall.com.

Transy’s PumpkinMania is a popular Lexington Halloween event.
Transy’s PumpkinMania is a popular Lexington Halloween event.

Transylvania PumpkinMania Festival begins

Come carve pumpkins 11 a.m. to 4 p.m. Oct. 29 at Transylvania University for the annual PumpkinMania display on the steps of Old Morrison facing Third Street, Oct. 29-Nov. 2. Free; go online to reserve a pumpkin. Food trucks will be on site, with tours of Rafinesque’s tomb and spooky tales on the lawn. Transylvania University, 300 N. Broadway, transy.edu/calendar/pumpkinmania

About 650 jack-o’-lanterns sit on display during PumpkinMania on the steps of the Old Morrison building at Transylvania University in Lexington, Ky., 2019. You can come carve one for the display, which opens Oct. 29.
About 650 jack-o’-lanterns sit on display during PumpkinMania on the steps of the Old Morrison building at Transylvania University in Lexington, Ky., 2019. You can come carve one for the display, which opens Oct. 29.

TAI on Rye pop-up Jewish deli

Get favorite Jewish foods including pastrami, corned beef sandwiches, kosher hot dogs, turkey salad, egg salad, tuna salad, chopped liver, matzo ball soup and baklava at this pop-up deli at Temple Adath Israel, 124 N. Ashland Ave. Dine in and carryout available. Noon to 2 p.m. Oct. 29. lextai.org

“Golden Girls” Drag Brunch at Rock House Brewing

Rock House Brewing will host a “Golden Girls” themed drag brunch on Oct. 29 from 11 a.m.-3 p.m. $15. 119 Luigart Ct. Eventbrite.com.

Lexington Community Orchestra Concert at Bryan Station High School

The Lexington Community Orchestra will perform a spooky symphonic fall concert at the Bryan Station High School Auditorium on Oct. 29 at 3 p.m. Free, but reservations are required. 201 Eastin Rd. LexingtonCommunityOrchestra.Weebly.com.

Todd Newton with a contestant during the “Price is Right” traveling show
Todd Newton with a contestant during the “Price is Right” traveling show

“The Price Is Right” Live! at Rupp Arena

“The Price Is Right” Live! Will give fans an opportunity to “Come On Down” and win prizes at Rupp Arena on Oct. 29 at 3 and 7 p.m. From $45. 430 W Vine St. RuppArena.com.

Hundreds of people participate in Lexington’s annual “Thriller” dance, parade and other Halloween events downtown.
Hundreds of people participate in Lexington’s annual “Thriller” dance, parade and other Halloween events downtown.

Halloween Variety Show & Thriller Parade

See a stage show on the Stephens Courthouse Plaza 5-6 p.m. with Halloween-inspired performances by Lexington area arts groups. Then enjoy Lexington’s Halloween Parade and Thriller reenactment, which has been named a Top 10 Halloween destination by “USA Today,” will take over the streets of downtown on Oct. 29 from 6:30-9 p.m. Free. 200 Main St. LexingtonKy.gov.