Best Lexington weekend events: Keeneland Fall Meet, Taylor Swift dance party, Freaky Flicks

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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, fall festivals, comedy shows, opera performances, University of Kentucky sports like volleyball and soccer, kid-friendly and free events and craft fairs.

Keeneland Fall Meet

Racing will return to Keeneland when its fall meet kicks off on Oct. 6 with the first call to post at 1 p.m. The 17-day fall meet runs Oct. 6-Oct. 28 with record prize money for racehorses and new wagering options. The track will offer $9.05 million in purses, including $5.55 million that will be awarded to during the opening Fall Stars Weekend, one of the biggest weekends in horse racing.

The Fall Stars Weekend, which will help determine the fields for the Breeders’ Cup World Championships in November at Santa Anita, also will have a new Breeders’ Cup Pick 6 wager this year. It will feature a total of six “Win and You’re In Races” – three from Keeneland and three from Santa Anita.

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 $7 on Wednesday and Thursday; $10 on Friday, Saturday and Sunday. It’s $15 for opening weekend. You can also buy a $50 season pass. You don’t need to buy tickets for the free tailgating area, The Hill, which is open Friday, Saturday and Sunday. It has a betting tent, jumbo TV, live music and food trucks. 4201 Versailles Rd. Keeneland.com.

There will be plenty to cheer about on opening weekend of the 2023 Keeneland Fall Meet. The racetrack will have new wagering options for race fans.
There will be plenty to cheer about on opening weekend of the 2023 Keeneland Fall Meet. The racetrack will have new wagering options for race fans.

Keeneland Fall Meet: Record purses, new wagering, tickets and dining options

After several horse deaths last spring, Keeneland begins Fall Meet. Where things stand.

Kentucky Wool Festival in Falmouth

The Kentucky Wool Festival will return to the Pendleton County hamlet of Falmouth from Oct. 6-8 with live music, sheep shearing and herding, a wool tent full of ready to spin fleeces, and more. $5-10, children under 6 free. 48 Concord Caddo Rd, Falmouth. KyWoolFest.org.

PAW Patrol Live! At Rupp Arena

Take the kids to see Ryder and his team of pups embark on a pirate-themed adventure to uncover hidden treasure when PAW Patrol Live! comes to Rupp Arena on Oct. 6 and 10 a.m. and 6 p.m. and Oct. 7 at 10 a.m., 2 and 6 p.m. From $20. 430 W Vine St. RuppArena.com.

PAW Patrol Live! “The Great Pirate Adventure” is a music-filled show based on the Nickelodeon animated TV show.
PAW Patrol Live! “The Great Pirate Adventure” is a music-filled show based on the Nickelodeon animated TV show.

Lexington Tree Week begins

The sixth annual Lexington Tree Week will begin Oct. 6 and run through Oct. 15 with a variety of events taking place around town. This weekend’s gatherings include everything from environmental board games at the Lexington Public Library to an Arbor Day celebration at the UK Arboretum, bird watching at Floracliff Nature Sanctuary and yoga at Ashland, the Henry Clay Estate. Ufi.Ca.Uky.edu/TreeWeek.

Freaky Flicks movie series at Masterson Station Park: ‘Hocus Pocus’

Start getting ready for Halloween with a showing of “Hocus Pocus” during the City of Lexington’s Freaky Flicks movie series at Masterson Station Park on Oct. 6 from 6:30-9:30 p.m. A Monster Mash dance party will kick things off prior to the movie starting at 7:30 p.m. Free. 3051 Leestown Rd. LexingtonKy.gov.

Haunted House tour at The Anderson Hotel

Explore a historically haunted Anderson Hotel in Lawrenceburg on Fridays and Saturdays from 7-11:30 p.m. through Oct. 31. One of the most haunted places in Kentucky, one walk through is sure to appease even the biggest horror fan’s delight for fright. $15. 116 S Main St, Lawrenceburg. OldAndersonHotel.com.

Fall Block Party at Greyline Station

Greyline Station will host a fall-themed block party on Oct. 6 from 5-9 p.m. with a bounce house, a face painter, pop-up shopping from over 50 small and local businesses, a DJ and more. 101 W Loudon Ave. facebook.com/events/678495530946676.

Comedian Kountry Wayne at Comedy Off Broadway

Comedian Kountry Wayne will perform at Comedy Off Broadway on Oct. 6 at 7 and 9:30 p.m., Oct. 7 at 6:30 and 9 p.m. and Oct. 8 at 7 p.m. $35-45. 161 Lexington Green Cir #C4. ComedyOffBroadway.com.

UK Opera Theatre’s ‘Susannah’ at the Lexington Opera House

The UK Opera Theatre kicks off its 2023-24 season with one of the most-performed American operas of all time, “Susannah”, at the Lexington Opera House on Oct. 6 at 7:30 p.m., Oct. 7 at 2 and 7:30 p.m. and Oct. 8 at 2 p.m. American composer Carlisle Floyd’s “Susannah,” is set in foothills of the Appalachian Mountains, telling a tale of a young woman who’s small mountain town turns against her after she is painted as a seductress by the church elders. Tickets start at $18. 401 W Short St. LexingtonOperaHouse.com.

“Susannah,” performed by the University of Kentucky Opera Theatre, is a story about Susannah Polk who’s small mountain town turns against her after she is painted as a seductress by the church elders for bathing in a creek near her home.
“Susannah,” performed by the University of Kentucky Opera Theatre, is a story about Susannah Polk who’s small mountain town turns against her after she is painted as a seductress by the church elders for bathing in a creek near her home.

Makaya McCraven concert at the Singletary Center

Genre-bending multi-instrumentalist Makaya McCraven will perform at the Singletary Center for the Arts on Oct. 6 at 7:30 p.m. $10-25. 405 Rose St. FineArts.Uky.edu.

Troubadour Concert Series: Shovels & Rope at the Lyric Theatre

The Troubadour Concert Series will present a concert from South Carolina based husband and wife duo Shovels & Rope at the Lyric Theatre on Oct. 6 at 7:30 p.m. $39.50. 300 E Third St. LexingtonLyric.com.

Wilmore Arts & Crafts Festival

The 24th annual Wilmore Arts & Crafts Festival will take place in the streets of downtown on Oct. 7 from 9 a.m.-4 p.m. with the best handmade goods available for purchase along with live music, children’s activities like pony rides from Asbury University, and more. 200 Rice St, Wilmore. facebook.com/events/730530211924028.

Millstone Festival in Downtown Richmond

The third annual Millstone Festival will bring a car show, live music, craft vendors, community booths, food trucks, a beer and wine garden, a kid’s area, inflatables, a petting zoo and more to the streets of downtown Richmond on Oct. 7 from 11 a.m.-8 p.m. Main St, Richmond. RichmondKy.us.

Roadworn Revival Festival in Stanford

Musicians Miles Miller, Clarke Sexton, Jordan Allen & The Bellwethers and others will perform during the second annual Roadworn Revival music festival at Englewood Estates in Lancaster on Oct. 7 beginning at 12 p.m. $35. 355 Engleman Rd, Lancaster. RoadwornRevival.com.

Sig Oktoberfest at Sig Luscher Brewery

Kentucky’s oldest brewery, Frankfort’s Sig Luscher, will again host its annual Oktoberfest celebrations from the capital city on Oct. 7 from 11 a.m.-10 p.m. For the day, Frankfort, Ky. will feel more like Frankfurt, Germany thanks to a variety of festive food trucks, Oktoberfest themed games and beers, live music from Kristofer Lee Bentley, among others, and more. Free. 221 Mero St, Frankfort. facebook.com/events/1005992324168791.

West Sixth Oktoberfest

West Sixth Brewing will hold day-long Oktoberfest celebrations at its Frankfort farm and Lexington and Louisville taprooms on Oct. 7 at noon. Festivities at its Lexington location will include German style beers, Bavarian eats from Smithtown Seafood, live music from the Wienerschnitzels, a giant pumpkin, a stein hoisting competition, a UK vs. Georgia football watch party and more. Reservations for a table seating 4-6 people start at $160 and come with six 0.5 liter steins to keep, 16 beer tickets, and an assortment of snacks. 501 W Sixth St #100. WestSixth.com/Oktoberfest.

During Oktoberfest at West Sixth Brewing, 1/2-liter steins will be available for beer and you can keep.
During Oktoberfest at West Sixth Brewing, 1/2-liter steins will be available for beer and you can keep.

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

Is this beer heaven? West Sixth farm has hops, hiking, tacos and yoga with goats

Bourbon On The Banks Festival at River View Park

Explore a variety of whiskeys, experience demonstrations and educational discussions from bourbon influencers, industry insiders, live music, bourbon-themed artisans and more when the Bourbon On The Banks Festival returns to River View Park in Frankfort on Oct. 7 from 2-6 p.m. $35-65. 404 Wilkinson Blvd, Frankfort. BourbonOnTheBanks.org.

Swiftie sing-a-long, dance party at Moondance Amphitheater

Listen to “Cruel Summer”, “Bad Blood” and other hits from Taylor Swift during a Swiftie sing-a-long at Moondance Amphitheater on Oct. 7 from 6-9 p.m. $5. 1152 Monarch St. LexingtonKy.gov.

Chords For Clark at the Leeds Center For The Arts

Choral music, barbershop quartets and comedy will fill the air when the seventh annual Chords For Clark benefiting the choirs of George Rogers Clark High School takes place at the Leeds Center for the Arts in Winchester on Oct. 7 from 7:30-9 p.m. $10-15. 237 N Main St, Winchester. Eventbrite.com.

Town Mountain concert at The Burl

North Carolina based country and bluegrass collective Town Mountain will perform at The Burl with support from Two Runner on Oct. 7 at 8 p.m. $18. 375 Thompson Rd. TheBurlKy.com.

Charcuterie & wine class at Harkness Edwards Vineyards

Learn how to make a Halloween-inspired charcuterie board while enjoying some of Harkness Edwards Vineyards’ signature wines during a workshop on Oct. 8 at 12 p.m. $57. 5199 Combs Ferry Rd, Winchester. facebook.com/events/242155571978039.

UK volleyball vs. Ole Miss at Rupp Arena

The UK volleyball squad will face off against the Ole Miss Rebels in SEC play at Rupp Arena on Oct. 8 at 1:30 p.m. $5-12. 430 W Vine St. UKAthletics.com.

UK women’s soccer vs. Vanderbilt at the Bell Soccer Complex

The UK women’s soccer team will take the field against the Vanderbilt Commodores at the Bell Soccer Complex on Oct. 8 at 3 p.m. $5-8. 556 Wildcat Ct. UKAthletics.com.

Harstad Fine Arts Series concert at Faith Lutheran Church

The Harstad Fine Arts Series will present “The King of Instruments and the Instrument of Kings”, a concert featuring trumpeter Chuck Seipp and pianist Randall Sheets, 3:30 p.m. Oct. 8. Free. 1000 Tates Creek Rd. HarstadArts.com.

Lexington Chamber Chorale concert at Second Presbyterian Church

Kentucky Bluegrass, the Italian Renaissance and Swedish contemporary music will join forces during the first concert of the Lexington Chamber Chorale’s 2023-24 season at Second Presbyterian Church on Oct. 8 at 5 p.m. $10-25. 460 E Main St. LexingtonChamberChorale.org.

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