Fall, Oktoberfest festivals, UK games highlight weekend events in, around Lexington

Matt Wickstrom
·5 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, Oktoberfest festivals and celebrations, food festivals, storytelling events, fall festivals, comedy shows, theatre plays, musicals and performances, University of Kentucky sports like football and soccer, kid-friendly and free events and a 10K race at Raven Run.

Oktoberfest Harrodsburg

Drawing nearly 15,000 patrons every year are Harrodsburg’s Oktoberfest celebrations, which aims to build upon those numbers when it reconvenes from Sept. 29-Oct. 1 in the streets of the Mercer County town. The event includes three days of live music from Danny Barnes & Friends, Bedford Band and others along with a kid’s zone and inflatables, adult games like cornhole and giant jenga, specialty foods and more. Free. 120 S Main St., Harrodsburg. OktoberfestHarrodsburg.com.

Oktoberfest In The Garden at Kentucky Native Cafe

Kentucky Native Cafe’s annual Oktoberfest in the Garden festivities will continue on Sept. 28 and 29 with live music from The Swells, Wienerschitzels Brass Band and more. They’ll also be serving fresh-baked Bavarian pretzels and will have plenty of German-inspired beer on tap from 4-10 p.m. daily. Free. 417 E Maxwell St. Michlers.com/Pages/Oktoberfest.

The annual Oktoberfest in the Garden at Kentucky Native Cafe behind Michler’s florists is a popular Fall event Lexington.
The annual Oktoberfest in the Garden at Kentucky Native Cafe behind Michler’s florists is a popular Fall event Lexington.

Looking for Oktoberfest festivals? Here are 12 in, around Lexington to raise a beer at

Harvest moon party at Harkness Edwards Vineyards

Celebrate the harvest moon at Harkness Edwards Vineyards in Winchester on Sept. 29 from 5-8 p.m. with live music from Lauren Mink and Dale Adams, tarot card readings, cooking classes with Sassy Ashley and more. Free. 5199 Combs Ferry Rd, Winchester. facebook.com/events/980495133230482.

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UK soccer double header vs. UCF and Alabama at the Bell

UK’s men’s and women’s soccer teams will host a double header on Sept. 29 at the Bell Soccer Complex with the men facing off against the University of Central Florida at 5 p.m. followed by the women battling the Alabama Crimson Tide at 7:30 p.m. $5-8. 556 Wildcat Ct. UKAthletics.com.

Cave Run Storytelling Festival in the Daniel Boone National Forest

Hear some top storytellers in the nation at the popular Cave Run Storytelling Festival, Sept. 29-30 on the shores of Cave Run Lake near Morehead. The storytelling performances will take place in two enormous tents at the Twin Knobs Recreational Area, which is part of the Daniel Boone National Forest. Tellers will be sure to have the audience’s attention and imagination and there will be ghost stories on Saturday night. Tickets, $5-$95; cash or check at the gate. caverunstoryfest.org

The Cave Run Storytelling Festival features some of the top storytellers from all over the country.
The Cave Run Storytelling Festival features some of the top storytellers from all over the country.

Love a good story? Kentucky festival talks to your imagination in unique setting

Comedian Trae Crowder at the Lexington Opera House

Comedian Trae Crowder will bring his “Just Me And Y’all” tour, originally scheduled for July 22 at the Lexington Opera House but postponed because of balcony ‘structural issues,’ on Sept. 29 at 8 p.m. From $29.50. 405 W Short St. LexingtonOperaHouse.com.

Lexington Theatre Company musical at Equus Run Vineyards

The Lexington Theatre Company will host two performances of the musical “Johnny & The Devil’s Box” at Equus Run Vineyards in Midway on Sept. 29 and 30 at 7:30 p.m. From $45. 1280 Moores Mill Rd, Midway. lexingtontheatrecompany.org.

A Boogie Wit Da Hoodie Concert at Rupp Arena

Bronx-born rapper A Boogie Wit Da Hoodie will bring his “Me VS. Myself: The College Tour” to Rupp Arena on Sept. 29 at 8 p.m. with special guests Toosii and Kaliii. From $41.75. 430 W Vine St. RuppArena.com.

Theatre play: The Studio Players ‘Ladies of Liberty’ at the Carriage House

The Studio Players will perform the World War II era “Ladies Of Liberty” at the Carriage House Theatre on Sept. 29 and 30 at 8 p.m. and Oct. 1 at 2:30 p.m. $15-22. 154 W Bell Ct. studioplayers.org.

Matt Stell concert at Manchester Music Hall

Multi-platinum country artist Matt Stell, known for hits like “Prayed For You” and “Everywhere But On”, will perform at Manchester Music Hall on Sept. 29 at 8 p.m. $12-50. 899 Manchester St. ManchesterMusicHall.com.

AfroLex Conference at the Lyric Theatre

The Marafiki Center’s third annual AfroLex Conference will take place at the Lyric Theatre on Sept. 30 from 10 a.m.-4 p.m. Networking and panel discussion topics include mental health and wellbeing, financial literacy, civic engagement, gun violence prevention and more. Free. 300 E Third St. Eventbrite.com.

UK Football vs. Florida at Kroger Field

The UK football team will look to go 2-0 in SEC play with a tilt against the University of Florida at Kroger Field on Sept. 30 at 12 p.m. From $85. 1540 University Dr. UKAthletics.com.

Kentucky fans stormed the field after their boisterous support during a Saturday night contest played a role in UK’s 20-13 upset of No. 10 Florida in 2021. Can Wildcats backers bring the same roar to this season’s noon kickoff vs. the No. 22 Gators?
Kentucky fans stormed the field after their boisterous support during a Saturday night contest played a role in UK’s 20-13 upset of No. 10 Florida in 2021. Can Wildcats backers bring the same roar to this season’s noon kickoff vs. the No. 22 Gators?

With Florida kickoff at noon, Saturday is a major test for Kentucky football fans

Grasstoberfest in Downtown Winchester

After first making its mark on Winchester last fall, Grasstoberfest will again pair Oktoberfest and bluegrass music in the streets of downtown on Sept. 30 from 2-11 p.m. with performances from Rumpke Mountain Boys, Reedy River String Band, and more. The fall festival event will also feature a BBQ cook off, a beer garden, artisan vendors, kids’ activities, a chicken dance and more. Free. 9 N Main St., Winchester. facebook.com/events/660221672650762.

Oktoberfest at Dreaming Creek Brewery

Richmond-based Dreaming Creek Brewery, which recently announced plans to expand into Berea, will host an Oktoberfest gathering on Sept. 30 at 2 p.m. Activities include live music from Will Ulmer and the A/C Unit along with a cornhole tournament, stein hoisting contest and food from the Spatzle Factory German Fare food truck. Free. 109 E Irvine St, Richmond. facebook.com/dreamingcreekbrewery.

Herman’s Hermits starring Peter Noone at the Lexington Opera House

The Lexington Opera House’s “Variety Live” season will conclude with a performance of “Herman’s Hermits” starring Peter Noone on Sept. 30 at 7:30 p.m. From $28.50. 405 W Short St. LexingtonOperaHouse.com.

Peter Noone and Herman’s Hermits will play Lexington Opera House.
Peter Noone and Herman’s Hermits will play Lexington Opera House.

Is the British Invasion back? Peter Noone and Herman’s Hermits will play Lexington

Nolan Taylor concert at The Burl

Cincinnati-based singer-songwriter Nolan Taylor, who recently signed to Atlantic Records, will perform an outdoor show at The Burl with support from Zach Bryan’s touring keyboardist, J.R. Carroll, on Sept. 30 at 8 p.m. $20. 375 Thompson Rd. TheBurlKy.com.

Raven 10K Trail Run at Raven Run Nature Sanctuary

The 9th annual Raven 10K Trail Run will take place at Raven Run Nature Sanctuary on Oct. 1 at 9 a.m. $30-45. 3885 Raven Run Way. LexingtonKy.gov.

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