Carson Kressley, WWE & more: The 16 best things to do in, around Lexington this weekend

By Matt Wickstrom Contributing writer

Updated October 1, 2021 9:42 AM

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 from live music concerts to the largest equine trade show and exhibition in North America at the Kentucky Horse Park, several Fall festivals including a few Oktoberfests, theatre plays, comedy shows, WWE wresting at Rupp Arena and more.

Alley Fest in Paintesville

The inaugural Alley Fest kicked off in downtown Paintesville Sept. 30. Ryan Hermens rhermens@herald-leader.com

The inaugural Alley Fest will take place on the streets of downtown Paintesville from Sept. 30-Oct. 2 with Americana, country, bluegrass and folk music from 49 Winchester, Nich Shoulders, Brit Taylor, Wayne Graham, Rachel Baiman and others. Tickets start at $30 with single day passes and move up to as much s $150 for a three-day VIP experience. 241 Main St, Paintesville. AlleyOnMainKy.com.

Boone Way Yard Sale

The Boone Way Yard Sale will take place along a 200 mile stretch of U.S. Route 25 that includes Crittenden, Georgetown, Richmond, Berea, Livingston, London, Corbin and more on Oct. 1 and 2. Hundreds of pop-ups are expected for the event, which is celebrating its 10th gathering after missing last year due to the pandemic. US25YardSale.com.

EQUITANA USA at the Kentucky Horse Park

EQUITANA USA, largest equine trade show and exhibition in North America, will be at the Kentucky Horse Park from Oct. 1-3 with 15,000-20,000 people attending. Carson Kressley from “Queer Eye for the Straight Guy” (a saddlebred owner and exhibitor) along with several current and former Olympians will be speaking. Events include product showcases, discussion panels with industry experts, EQUUS Evolution theatrical productions, kids activities, show jumping and dressage exhibitions; and more. Single day tickets cost up to $27 while three-day passes run up to $70. 4089 Iron Works Pkwy. EquitanaUsa.com.

Greyline Station Block Party

The inaugural Greyline Block Party will take place on Oct. 1 from 5-9 p.m. with pop-up vendors (to go along with those already inside the Julietta Market), a Farmer’s Market in collaboration with Black Soil and a DJ. The event is free to attend. 101 W Loudon Ave. facebook.com/events/399509948259103.

Harrodsburg Oktoberfest

The 5th Harrodsburg Oktoberfest will take place along the town’s Main Street from Oct. 1-3 with free concerts, food and art vendors, kid’s activities and more. Festivities will take place on Oct. 1 from 5 p.m.-midnight, Oct. 2 from 10 a.m.-midnight and Oct. 3 from 12-6 p.m. S Main Street, Harrodsburg. OktoberfestHarrodsburg.com.

Cumberland Mountain Fall Festival

The Cumberland Mountain Fall Festival will return to the streets of downtown Middlesboro on Oct. 1 and 2 with music from Lucero, Morgan Wade, Magnolia Boulevard, Joslyn & The Sweet Compression, Logan Halstead and more. The event also includes a car show, kid’s pageant and activities, food and craft vendors and more. The event is free to attend. 221 N 21st St., Middlesboro. CumberlandMountainFallFestival.net.

Versailles Oktoberfest / Mini Art In The Park

The Versailles Merchant Association will host the first ever Oktoberfest in downtown Versailles on Oct. 1 from 6-9 p.m. The free to attend event includes food, drinks and live music with The Pour Decisions. Green Street, Versailles. facebook.com/events/1040606963140632. At the same time as Oktoberfest, The Art Village is gathering at nearby Big Springs Park for a Mini Art In The Park. The event will have local artisans and Oktoberfest-themed food and beverage options. It is also free to attend. 140 Park St, Versailles. facebook.com/events/1184131865426813.

Rye Davis, Cole Chaney concert at Austin City Saloon

Western Kentucky songwriter Rye Davis (Pig, Ky.) and Eastern Kentucky artist Cole Chaney (Ashland, Ky.) will perform at Austin City Saloon on Oct. 1 at 7 p.m. Tickets are $10 plus fees. You must be 21 or older to attend. 2350 Woodhill Dr. Austincitysaloon.com.

Wilmore Arts and Crafts Festival

The Wilmore Arts and Crafts Festival will gather for the 23rd time on Oct. 2 from 9 a.m.-4 p.m. with over 50 vendors selling wood crafts, knitted and crocheted items, candles, soap, shaker boxes, wreaths, farmhouse signs, jewelry, baskets and more. The event is free to attend. 335 E Main St., Wilmore. facebook.com/events/319631452793974.

West Sixth Oktoberfest

West Sixth Brewing will celebrate Oktoberfest at its flagship Lexington location on Oct. 2 from 12-10 p.m. with specialty beers, giant pumpkins, big steins. The event is free to attend. 501 W Sixth St, #100. westsixth.com/oktoberfest.

Lyric monthly take home program pick-up

The Lyric Theatre, in partnership with Black Soil, will be distributing the Halloween-themed October edition of it’s “FAM: Family. Art. Memories” free, take home programs on Oct. 2 from 1-4 p.m. A limited number of 40 programs are available on a first come first served basis. This month’s pickup will be conducted from the Lyric’s theatre entrance instead of the Cultural Arts Center due to construction. 300 E Third St. facebook.com/events/170110065231148.

Kentucky Reptile Expo

Get an up close look at a variety of reptiles, amphibians, spiders, insects and more during the Kentucky Reptile Expo at the Central Bank Center on Oct. 2 from 10 a.m.-4 p.m. Tickets are $7. 430 W Vine St. Kentuckyreptileexpo.com.

Trevor Wallace at Comedy Off Broadway

Comedian Trevor Wallace, also known for his YouTube videos, will perform six shows at Comedy Off Broadway from Sept. 30-Oct. 3, $25-45. 161 Lexington Green Cir #C4. ComedyOffBroadway.com.

Lexington Children’s Theatre play: ‘Shoyu Tell’

Rusty Allen, left, playing Lucas, and Kim Dixon, playing Emily, rehearse for “Shoyu Tell” which has its world premiere this weekend at the Lexington Children’s Theatre. The story is about a Japanese-American student whose lunchbox contents makes him the target of the school bully. Ryan C. Hermens rhermens@herald-leader.com

The Lexington Children’s Theatre will premiere ‘Shoyu Tell,’ a play about Japanese-American bullying experience using anime and video game visual elements. Showtimes are 2 and 7 p.m. Oct. 2, 2 p.m. Oct. 3. Tickets are $15-$20 with the 7 p.m. Oct. 2 showing a pay-what-you-will performance. lctonstage.org

Restless Leg String Band concert at The Burl

Restless Leg String Band will perform a hometown show at The Burl, their last with original bassist Joe Schlaak prior to his departure from the group, on Oct. 2 at 9 p.m. Tickets are $13 plus fees. 375 Thompson Rd. TheBurlKy.com.

WWE Supershow at Rupp Arena

World Wrestling Entertainment returns to Rupp Arena with the WWE Supershow on Oct. 3 at 7 p.m. The event includes bouts with Universal Champion Roman Reigns, WWE Champion Big E, Smackdown Women’s Champion Becky Lynch, Smackdown Tag Team Champions The Usos, and more. Tickets are $20-175. RuppArena.com.

Matt Wickstrom is a freelancer covering food, music and more. You can follow him on Instagram at @WickstromWrites.

This story was originally published October 1, 2021 at 6:00 AM.