October Plan Ahead: Your Lexington events calendar

Is that the call to post we hear?

From tailgates to Oktoberfests — we’re excited for all the events to kick off the changing of seasons (Keeneland, anyone?). Read on for a highlight of top events that are happening this month in Lex. We’ve also linked out to our full October Plan Ahead below, so you can go ahead and add to calendar.

Friday, Oct. 1

• Music on the Lawn at Shaker Village | Fri., Oct. 1 | 6:30 p.m. | Shaker Village, 3501 Lexington Road | Free | Live music on the lawn, outdoor dining, and specialty cocktails around the firepit. 🎶
• Fall Festival + Oktoberfest Block Party | Fri., Oct. 1 | 5 p.m. | Greyline Station | Free | Live music from DJ Nerddboi, pop-up vendors, and pumpkin decorating 🍺
• Oktoberfest Harrodsburg 2021 | Fri., Oct. 1 - Oct. 3 | All weekend | Main St., Harrodsburg | Free | This is one of Kentucky’s largest Oktoberfests featuring music, food, beer, crafts, and family-friendly activities. 🍺
• Boy Band Review | Fri., Oct. 1 | 7 p.m. | Tin Roof | Free | Boy Band Review will transport you back in time to the days of frosted tips and hunky frontmen professing their undying love. 🎤
• Oktoberfest in Versailles | Fri. Oct. 1 | 6-9 p.m. | Green St., Versailles | Free | Hosted by the Versailles Merchant Festival. Enjoy food, drinks, and live music downtown. 🍂
• Mini Art in the Park | Fri. Oct. 1 | 6-9 p.m. | The Woodford Inn | Free | Browse arts + crafts from local artisans while enjoying Oktoberfest-themed food and drinks. 🎨
• Fall Festival & Oktoberfest Bloc Party | Fri. Oct. 1 | 5-9 p.m. | Greyline Station | Free | Fall festivities at Lexington’s hip public market. 🎃

Saturday, Oct. 2

• Kentucky Wildcats Football vs. Florida Gators | Sat., Oct. 2 | 6 p.m. | Kroger Field | $55 | The Cats take on the Gators for a heated rivalry game at home. 🏈
• Lawrenceburg Ghost Walk | Sat., Oct. 2 | 8 p.m. | The Mix, Lawrenceburg | $10 | Explore downtown Lawrenceburg while learning about the town’s paranormal (and normal) history. 👻
• Fall Festival Arts + Craft | Sat., Oct 2 | 1 p.m. | Fairhaven Baptist Church, 2265 Liberty Rd. | Free | Enjoy this fall festival that will have food + shopping from local vendors. 🎨
• Hoptoberfest | Sat., Oct 2 | 2 p.m | Mountain Top Media Stage, Pikeville | 2 p.m. | $30 | Enjoy craft beer in a mountain setting at Pikeville’s annual craft beer festival. 🍻
• Oktoberfest at The Grove | Sat., Oct 2 | All Day | The Grove | Free | Enjoy themed food and local Oktoberfest beers in the beer garden. 🍻
• Pumpkin Jamboree | Sat., Oct. 2 | 10 a.m.-5 p.m. | Eckert’s Orchard | $5 | Live entertainment, festival food, wagon + camel rides, and fun for kids of all ages. 🎃
• Ladies Day Out | Sat., Oct. 2 | 10 a.m.-4 p.m. | Embassy Suites at Coldstream | Free | A day of pampering with a variety of health + beauty vendors.
• Wilmore Arts & Craft Festival | Sat., Oct. 2 | 9 a.m. | Main St., Wilmore | Free | Explore downtown shops and treasure hunt from the over 50 vendors.

Sunday, Oct. 3

• WWE Supershow | Sun., Oct. 3 | 7 p.m. | Rupp Arena | $33+ | This is a show that’s sure to pack a punch. 👊
• Fire Prevention + Wellness Festival | Sun., Oct. 3 | 2-6 p.m. | Masterson Station Park | Free | Fire truck rides, fire safety demonstrations, food, games + more. 🚒
• The Raven 10K | Sun., Oct. 3 | 9 a.m. | Raven Run Nature Sanctuary | $45 | Get outside and get your heart pumping in this trail race benefitting the Raven Run Education Program. 🏃‍♀️
• Tree Identification Nature Walk | Sun., Oct. 3 | 1:30 p.m. | McConnell Springs | Free | Kick off Tree Week with a walk in the woods with Dr. Melinda Wilder. 🌳
• Pumpkin Jamboree | Sun., Oct. 3 | 10 a.m.-5 p.m. | Eckert’s Orchard | $5 | Live entertainment, festival food, wagon + camel rides, and fun for kids of all ages. 🎃
• Alex Mason Gallery Talk | Sun., Oct. 3 | 1:30 p.m. | Headley-Whitney Museum | $10 | View the “Informed by Nature” collection + learn about the process from featured artist Alex Mason. 🎨

Oct. 4 - Oct. 10

Monday, Oct. 4

• Woodsongs Old-Time Radio Hour | Mon., Oct. 4 | 6:45 p.m. | The Lyric Theatre | $10 | Enjoy music from “The Ambassador of Blues,” Guy Davis. 🎵
• Trivia at Wisebird Cider Co. | Mon., Oct. 4 | 7 p.m. | Wisebird Cider Co. | Free | Choose your teammates wisely because there are cash prizes to win. 💵

Tuesday, Oct. 5

• Bluegrass Farmers’ Market | Tues., Oct. 5 | 2-5 p.m. | Liquor Barn in Hamburg | Free | Support your local farmers + pick up your veggies 🍅
• Buffalo Nichols | Tues., Oct. 5 | 8 p.m. | The Burl | $15 | Blues at the Burl with Buffalo, trying saying that 5 times fast. 🎸

Wednesday, Oct. 6

• Yin Yoga at The Apiary | Wed., Oct. 6 | 8-9 a.m. | The Apiary, | $20 | Get your zen on with a relaxing yin class taught by Lissa Sims 🧘‍♀️
• WLK Roundtable Networking Luncheon | Wed., Oct. 6 | 12-1:30 p.m. | The Grand Reserve | $39 | Guest speaker will be Sylvia Lovely, Founder of Connecting our Voices. 🎤
• Springhouse Music Series | Wed., Oct. 6 | 5-9 p.m. | Castle & Key Distillery | Free | Grab a chair + a friend to enjoy the final night of this series. 🎵
• Yoga & Brews | Wed., Oct. 6 | 7 p.m. | Ethereal Brewing Company | Free | Slow down, find peace + enjoy craft beer. 🍺
• Studio 300 Digital Art and Music Festival | Wed., Oct. 6 | Hours vary | Transylvania University | Free | A festival dedicated to the cutting edge of creativity featuring concerts, art exhibitions, artist talks + an online gallery. 🎨

Thursday, Oct. 7

• UK Women’s Soccer vs. Vandy | Thurs., Oct. 7 | 7 p.m. | Wendell & Vickie Bell Soccer Complex | Free | Men’s + women’s home soccer games are all free this season. ⚽
• Veterans Art Competition | Thurs., Oct. 7 |10 a.m.-6 p.m.| Central Library Gallery | Free | Support local Navy + Army veterans whose artwork could wind up at the national competition.🖌
• Studio 300 Digital Art and Music Festival | Wed., Oct. 6 | Hours vary | Transylvania University | Free | A festival dedicated to the cutting edge of creativity featuring concerts, art exhibitions, artist talks + an online gallery. 🎨

Friday, Oct. 8

• Keeneland Fall Meet Begins | Fri., Oct. 8-Sat., Oct. 30 | Times vary | Keeneland | Prices vary | Back open at full capacity with added entertainment on The Hill. 🏇
• Contemplation Hike | Fri., Oct. 8 | 4 p.m. | Floracliff Nature Sanctuary | $10 | Kick off Tree Week with a contemplation walk through the Floracliff forest + learn more about the roles of trees and relationships they support. 🍂

Saturday, Oct. 9

• For King & Country | Sat., Oct. 9 | 7 p.m. | Rupp Arena | $28.50 | King + Country are coming to the big stage for their Fall 2021 Tour 🎸
• Pride Run 5k | Sat., Oct. 9 | 9 a.m. | Coldstream Park | $30 | A 1-mile fun walk option will also be available with awards given for 13 age groups and three gender categories. 👟
• Barktoberfest | Sat., Oct. 9 | 11 a.m. | Liquor Barn, Hamburg | Free | Music, arts, and food with all proceeds going to help the homeless and injured critters of KY. 🐶
• South Elkhorn Fall Festival | Sat., Oct. 9 | 9 a.m. | South Elkhorn Christian Church, 4343 Harrodsburg Rd. | Free | One of the largest outdoor free craft shows with over 150 booths. 🍂
• Pumpkin Jamboree | Sat., Oct. 9 | 10 a.m.-5 p.m. | Eckert’s Orchard | $5 | Live entertainment, festival food, wagon + camel rides, and fun for kids of all ages. 🎃

Sunday, Oct. 10

• Books + Brews Book Club | Sun., Oct. 10 | 7 p.m. | Virtual | Free | Grab a drink and drop in to discuss this month’s selection, The Sun Down Motel by Simone St. James. 📚
• Pumpkin Jamboree | Sun., Oct. 10 | 10 a.m.-5 p.m. | Eckert’s Orchard | $5 | Live entertainment, festival food, wagon + camel rides, and fun for kids of all ages. 🎃
• Our Town | Sun., Oct. 10 | 2:30 p.m. | Leeds Center for the Arts, Winchester | $15 + | Enjoy a matinee showing of Our Town which has been dubbed, “The greatest American play ever written.”

Oct. 11 - Oct. 17

Monday, Oct. 11

• Tee It Up For The Kids | Mon., Oct. 11 | 11 a.m. | Griffin Gate Golf Club | Prices Vary | Support The Foster Care Council with a day on the links + silent auction. ⛳
• Genealogy 101 | Mon., Oct. 11 | 6 p.m. | Paris-Bourbon County Library | Free | Learn the basics of genealogy + maybe something about your heritage. 📚

Tuesday, Oct. 12

• Thoroughbred Makeover | Tues., Oct. 12-Sun., Oct. 17 | 8 a.m.-5 p.m. | Kentucky Horse Park | Free | See the world’s largest thoroughbred retraining competition for recently-retired racehorses. 🐎
• Bourbon + History Walking Tour | Tues., Oct. 12 | 1 p.m. | 300 Saint Clair St., Frankfort | $11 | Learn about our state capital’s spirited bourbon history on this 1-hour tour through their scenic downtown. 🥃
• Paint + Sip | Tues., Oct. 12 | 6:30 p.m. | Pinot’s Palette | $27 | Grab your friends for a paint + sip night featuring a fun rustic chalkboard pumpkin theme.
• Small Trees for Urban Landscapes | Tues., Oct. 12 | 5:30 p.m. | Idle Hour Neighborhood, 124 Idle Hour Dr. | Free | A 1-hour walk through the Idle Hour neighborhood will showcase 10-15 plants used in local landscaping.

Wednesday, Oct. 13

• Murder Mystery Dinner on the Rooftop | Wed., Oct. 13 | 7-9 p.m. | The Kentucky Castle, 230 Pisgah Pike | $85 | Dine on the rooftop + figure out whodunnit. 🔍
• Launchpad Lex Speaker Series: Entrepreneurship | Wed., Oct. 13 | 5 p.m. | Ethereal Brewing | Registration Required | Opportunity for entrepreneurs, small businesses, and founders to come together, share ideas, and build connections 🏙️
• Pumpkin Carving Party | Wed., Oct. 13 | 4-8:30 p.m. | GirlsGirlsGirls Burritos, 395 S. Limestone | Free | Apple cider, chili + free pumpkins provided by Black Soil Ky
• Comedy Night at Ethereal Brewing | Wed., Oct. 13 | 8 p.m. | Ethereal Brewing, Distillery District | Free | Comedy and craft beer with CMT’s Next Big Comic finalist Kelly Collette
• Art by Nature Gallery Reception | Thurs., Oct. 14 | 5-7 p.m. | Julietta Market | Free | Enjoy light refreshments + music while viewing the tree-themed art exhibit.

Thursday, Oct. 14

• Tree Week Golden Hour Hike | Thurs., Oct. 14 | 5-7 p.m. | Floracliff Nature Sanctuary | Free | Relax with a quiet sunset hike. 🌅
• Barrel House Distillery Tours | Thurs., Oct. 14 | 11 a.m.-4 p.m. | Distillery District, 1200 Manchester Street | $7.84 | You can sample products while learning about Lexington’s rich distilling heritage and review the distilling process. 🥃
• Doyle Lawson and Quicksilver | Thurs., Oct. 14 | 7-8:30 p.m. | The Kentucky Castle | $45+ | Enjoy a pre-show cocktail hour with a VIP ticket + enjoy music from the Grammy-winning bluegrass singer.
• UK versus LSU | Thurs., Oct. 14 | 7 p.m. | Free | Wendell & Vickie Bell Soccer Complex | UK women’s soccer takes on LSU at home. ⚽

Friday, Oct. 15

• The Mountain Goats | Fri., Oct. 15 | 8-12 p.m. | Manchester Music Hall | $26 | Listen to the indie folk giant live with their newest album. 🪕
• 80’s Night w/ Vinyl Richie | Fri., Oct. 15 | 7 p.m. | The Burl | $12 | Travel back in time for this 80’s retro costume party.
• Big Blue Madness | Fri., Oct. 15 | 7 p.m. | Rupp Arena | Free | Meet this year’s men’s and women’s lineup, and preview their dance moves, at this fan-favorite event 🏀
• Curator Tour | Fri., Oct. 15 | 6-7 p.m. | UK Art Museum | Free | Register for this guided tour of After, a three-gallery installation. 🖼️
• Secretariat Festival | Fri., Oct. 15 - Sun., Oct. 17 | Kentucky Horse Park | Prices TBD | This festival includes horse farm tours, celebrity appearances, and a big Friday night kick-off party. 🐴
• PRHBTN Gallery Opening | Fri., Oct. 15 | 6 p.m. | The Loudoun House | Free | Kick off the 10th Annual PRHBTN Gallery with a cash bar + food trucks while checking out the work of 100+ Kentucky artists.

Saturday, Oct. 16

• Trunk-or-Treat | Sat., Oct. 16 | Regal Cinemas Hamburg | Free, but registration required | Face painting, food trucks, character meet + greets, and of course, trick-or-treating.
• Candle Making Workshop | Sat., Oct. 16 | 10 a.m. - 2 p.m. | $50 | Enjoy a boxed lunch — included in the ticket price — and learn how to make your own dipped candles. 🕯️
• Family Day Art Construction | Sat., Oct. 16 | 12 p.m. | UK Art Museum | Free | Families are invited to test their artistic skills to build + create with the supplies they are provided.
• Music at Wildside Winery | Sat., Oct. 16 | 1 p.m. | Wildside Winery | Free | Enjoy live tunes in the tasting room from local musician Matt Castle
• Compost Workshop | Sat., Oct. 16 | 9:30 a.m.-12 p.m. | Free | McConnell Springs | By attending this workshop you’ll be able to enroll in the city’s new compost pilot program.
• Sunrise Trackside | Sat., Oct. 16 | 8-10:30 a.m. | Free | Grab coffee + donuts while watching the horses train and enjoy family-friendly activities with Keeneland’s mascot, Buckles.
• Spooky Thrifts | Sat., Oct. 16 | 12 p.m. | Rockhouse Brewing | Free | A Halloween pop-up with curated vintage clothing.
• Family Dog | Sat., Oct. 16 | 10 p.m. | Henry Clay Public House | Free | Live music featuring Family Dog

Sunday, Oct. 17

• Bad Bad Hats | Sun., Oct. 17 | 7 p.m. | The Burl | $10 | Jam out to the Twin Cities-based indie rock trio. 🎸
• The Grove Halloween Drag Brunch | Sun., Oct. 17 | 11 a.m. | The Grove | $20 | Brunch, glitter, fabulous drinks + a drag show performance by Scarlett Moon and her Queens. ✨
• Alano Classic Tee Off Dinner | Sun., Oct. 17 | TBD | The Campbell House | $75 | Live music, silent auction, and mingling with celebrities to kick off the Alano Classic Golf tournament.
• Halloween Watercolor Class | Sun., Oct. 17 | 1 p.m. | Pivot Brewing | $35 | Brush op on your watercolor skills while painting spooky-themed Halloween banners + sipping craft beer.

Oct. 18 - Oct. 24

Monday, Oct. 18

• Mother Goose Storytime | Mon., Oct. 18 | 11:30 a.m.-12:15 p.m. | Jessamine County Public Library | Free | Storytime + sing-a-long rhymes for you and your little one, registration is required.
• Friends Book Cellar | Mon., Oct. 18 | 10 a.m.-4 p.m. | Central Library, Downtown | Free | Find your new favorite read at the Friends of the Public Library book sale.
• Hallowed Moon | Mon., Oct. 18 | 6:30 p.m. | Pinot’s Palette | $35 | Sip on a glass of wine and perfect your paint skills as you practice painting the harvest moon. 🌕

Tuesday, Oct. 19

• Bluegrass Farmers Market | Tues., Oct. 19 | 2-5 p.m. | Liquor Barn, Hamburg | Free | Shop for Kentucky proud fruits, vegetables, canned goods, honey, and flowers. 🌽
• Concert for a Cure | Tues., Oct. 19 | 7 p.m. | The Lyric Theatre | $30 | Enjoy live music from the American Authors, Wrabel, and more in support of Breast Cancer Awareness Month. 🎵
• UK Chorale Concert | Tues., Oct. 19 | 7:30 p.m. | Singletary Center | Price TBD | Enjoy vocal performances from the UK Chorus who will be joined by Lexington Christian Academy’s choir.

Wednesday, Oct. 20

• The Marcus King Band | Wed., Oct. 20 | 8 p.m. | Manchester Music Hall | $25 | The Marcus King Band + Leah Blevins 🎸
• UK Symphony Band and UK Concert Band | Wed., Oct. 20 | 7:30 p.m. | Singletary Concert Hall | Free | Free tunes from UK’s School of Music
• Karaoke | Wed., Oct. 20 | 9 p.m. | Tin Roof | Free | Brave the stage with the help of drink specials
• Castle & Key Cocktail Dinner | Wed., Oct. 20 | 6:30 p.m. | The Thirsty Fox | $50 | Enjoy a 3-course meal from Chef Ethan Bowling paired with cocktails from Castle & Key’s new line.
• Nick Shoulders | Wed., Oct. 20 | 8 p.m. | The Burl | $15 | Enjoy pinball + live music at The Burl with Nick Shoulders + Todd Day Wait
• Open Mic Night | Wed., Oct. 20 | 7 p.m. | Brewed, 124 Malibu Dr. | Free | All talents are welcome — comedy, music, magic + more.

Thursday, Oct. 21

• Friends of the Red River Gorge | Thurs., Oct. 21 | 6 p.m. | J&H Lanmark | Free | Learn about beginner trails + important news from Red River Gorge executive director Dave McCreary.
• Hocus Pocus Trivia | Thurs., Oct. 21 | 7 p.m. | Rock House Brewing | Free | Sip on craft beer + test your Sanderson sister knowledge.
• Country Boy + West Sixth Tap Takeover | Thurs., Oct. 21 | 2 p.m. | Shamrock Bar & Grille, Georgetown | A tap takeover featuring two of Lexington’s favorite breweries with trivia at 8:30 p.m.

Friday, Oct. 22

• The Scarefest | Fri., Oct. 22-Sun., Oct. 23 | Times vary | Central Bank Center | $25+ | Visit the horror convention + film fest for its 13th year. 🦇
• Friday Night Music | Fri., Oct. 22 | 6-8 p.m. | Windy Corner Market | Free | Dine + listen to local musicians on the back patio among the hills of horse country.
• Blue-White Game | Fri., Oct. 22 | 7 p.m. | Rupp Arena | Prices TBD | Get a preview of this year’s squad in the annual preseason scrimmage. 🏀
• Black Soil Farm-to-Table Tasting | Fri., Oct. 22 | 6 p.m. | $80 | A collaborative dinner event featuring a fresh local 3-course dinner with Castle & Key cocktail pairings.
• Dillon Carmichael | Fri., Oct. 22 | 8 p.m. | $20+ | The Lexington native returns bringing his country music hits.
• UK vs. Arkansas | Fri., Oct. 22 | 9 p.m. | Memorial Coliseum | $8 | The No. 5 Kentucky Volleyball team will host the Arkansas Razorbacks this weekend for a two-match Southeastern Conference series.
• Redistricting Bingo | Fri., Oct. 22 | 7 p.m. | RSVP | Greyline Station | Learn about Redistricting in a fun and social way — with Bingo.

Saturday, Oct. 23

• Jason Aldean | Sat., Oct. 23 | 7:30 p.m. | Rupp Arena | $53+ | The 2021 Back in the Saddle Tour featuring Hardy + Lainey Wilson 🎸
• Emo Night Tour | Sat., Oct. 23 | 8 p.m. | The Burl | $12 | Relive the aughts at this 21+ emo punk blowout. 🤘
• Pumpkin Jamboree | Sat., Oct. 23 | 10 a.m.-5 p.m. | Eckert’s Orchard | $5 | Live entertainment, festival food, wagon + camel rides, and fun for kids of all ages. 🎃
• Beer + Chili Cook-off | Sat., Oct. 23 | 5 p.m. | Greyline Station | Prices vary | Beer, chili + entertainment with proceeds going to benefit Black Soil Ky
• Trunk-or-Treat | Sat., Oct. 23 | 2-4 p.m. | Whitaker Family YMCA | Free | A trunk-or-treating event featuring a costume contest + pumpkin decorating
• Lemon & Lavender Market | Sat., Oct. 23 | 10 a.m.-5 p.m. | Bluegrass Hall, 3000 Elizabeth St., Nicholasville | $5 | Enjoy a fun day of shopping featuring handmade jewelry, paintings, and antiques.
• Trunk-or-Treat | Sat., Oct. 23 | 2-4 p.m. | Whitaker Family YMCA | Free | A trunk-or-treating event featuring a costume contest + pumpkin decorating
• UK vs. Arkansas | Sat., Oct. 22 | 7 p.m. | Memorial Coliseum | $8 | The No. 5 Kentucky Volleyball team will host the Arkansas Razorbacks this weekend for a two-match Southeastern Conference series.

Sunday, Oct. 24

• White Reaper | Sun., Oct. 24 | 8 p.m. | The Burl | $20 | Louisville’s White Reaper is coming to Lexington to party, rock out + and have a good time. 🎸
• Mummy Cake Decorating | Sun., Oct. 24 | 2-4 p.m. | Pivot Brewing | $45 | Create 4 different mummy cupcakes and sip delicious beers. 1 drink ticket is included. 🧁
• Pumpkin Jamboree | Sun., Oct. 24 | 10 a.m.-5 p.m. | Eckert’s Orchard | $5 | Live entertainment, festival food, wagon + camel rides, and fun for kids of all ages. 🎃
• Cider and Food Pairing | Sun., Oct. 24 | 4 p.m. | Pivot Brewing | $20 | Pivot Brewing + Laura Lou Patisserie team up to pair craft ciders and sweet treats.
• UK versus UM | Sun., Oct 24 | 2 p.m. | Wendell & Vickie Bell Soccer Complex | Free | UK women’s soccer takes on the University of Missouri.
• Tunes in the Vines | Sun., Oct. 24 | 2-4:30 p.m. | Equus Run Vineyards | Free | A bottle of wine, good friends, and great local music are the perfect blend for Sunday afternoons.
• Country Boy Chili Cookoff | Sun., Oct. 24 | 1-5 p.m. | Country Boy Brewery | Free | Eat well and do good by bringing a canned good for God’s Pantry.
• Trunk-or-Treat | Sun., Oct. 24 | 7 p.m. | Douglas Park | Sponsored by Lexington Black Professional Firefighters

Oct. 25 - Oct. 31

Monday, Oct. 25

• Bilingual Story Time | Mon., Oct. 25 | 11 a.m. | Free | Northside Library | Bring your preschoolers to learn about communication with Flavia Z. Drago. 📖
• Old-Time Jam Session | Mon., Oct. 25 | 6 p.m. | Free | Broomwagon | Watch, listen or jam along at this free old-time music jam. All levels and all instruments welcome. 🪕

Tuesday, Oct. 26

• UK versus Bellarmine | Tue. Oct. 26 | 7 p.m. | Free | Wendell & Vickie Bell Soccer Complex | The men’s soccer team takes on the Knights at home. ⚽
• Ag is for All | Tue. Oct. 26 | All day | 9 a.m.-3 p.m. | Geared towards high school students, this conference gives a deep dive into UK’s College of Agriculture, Food and Environment.
• SASAMI w/ Wombo | Tue. Oct. 26 | 8 p.m. | The Burl | $12 | The Los Angeles native is bringing her orchestral-rock sound to Lexington.
• Side Hustle Accelerator | Tue. Oct. 26 | 3 p.m. | Virtual | Registration Required | Learn to monetize your side hustle + take it to the next level

Wednesday, Oct. 27

• Houseplant Swap | Wed., Oct. 27 | 5-7 p.m. | The Fishtank, 500 Euclid Ave. | Free | Bring your plants, pots + cuttings and trade up your collection. 🪴
• Castlewood Halloween | Wed., Oct. 27 | 4-7 p.m. | Castlewood Park | Free | A neighborhood trick-or-treating event sponsored by West Sixth Brewery + Kentucky For Kentucky
• The Rocky Horror Picture Show | Wed., Oct. 27 | 8:30 p.m. | Soundbar | Free | Dressup + sing-a-long to a Halloween classic with themed karaoke to follow the film.
• Jack-o-lantern Trail | Wed., Oct. 27 | 6:30 p.m. | McConnell Springs | $5 | Hike through McConnell Springs to enjoy hundreds of hand-carved pumpkins.

Thursday, Oct. 28

• Bourbon Pairing Dinner | Thurs., Oct. 28 | 7-9 p.m. | The Kentucky Castle | $150 | Enjoy a four-course farm-to-table dinner + a guided selection of bourbon. 🥃
• Ghost Tea at Waveland | Thurs., Oct. 28 | 6:30-8:30 p.m. | Waveland State Historic Site | $40 | Tour Waveland by candlelight for a haunting tea party. Costumes or black clothing required. ☕
• A Very Masked Murder Mystery Dinner | 7 p.m. | Goodwood | $48 | Masks, mayhem + murder rule the evening at this fun charity event featuring dinner and a show.
• UK Men’s Chorus + Women’s Choir | Thurs., Oct. 28 | 7:30 p.m. | Singletary Recital Hall | $10 | Also featuring acoUstiKats + Paws and Listen
• Parent Survival Night | Thurs., Oct. 28 | 6-10 p.m. | The Little Gym of Lexington East, 3101 Richmond Rd. | $35 | Let the kids run around + play while you have a parents-night-out.

Friday, Oct. 29

• Monster Bash Gala | Fri., Oct. 29 | 7 p.m. | Limestone Hall | $125 | Prizes await for best costume while you enjoy food, music and dancing in support of the Blue Grass Farms Charities. 🧟‍♀️
• Halloween Murder Mystery Dinner | Fri.., Oct. 29 | 7-9 p.m. | The Kentucky Castle | $130 | Dine on the rooftop + figure out whodunnit. 🔍
• Dia de los Muertos | Fri., Oct. 29 | 7 p.m. | Lexington Opera House | A beautiful production about life + death starring the Bluegrass Youth Ballet.
• UK MBB versus Kentucky Wesleyan College | Fri., Oct. 29 | 7 p.m. | Rupp Arena | $100 | The Cats first home game of the season is sure to be a fun one. 🏀

Saturday, Oct. 30

• Oktoberfest Horse Trials, Combined Test, and Dressage Show | Sat., Oct. 30-Sun., Oct. 31 | 8 a.m. | Kentucky Horse Park | Prices vary | Get spooky with this entry-level competition, trade fair + costume contest. 🐴
• Spooktacular: A Family Friendly Festival | Sat., Oct. 30 | 5-8 p.m. | LexCity Church | Free | Register for this family friendly Halloween parade. 🎃
• Soundbar’s Halloween Party 2021 | Sat., Oct. 30 | 8 p.m. | Soundbar | $10+ | Suit up for Soundbar’s biggest party of the year. 🕸️
• Halloween Bar Crawl | Sat., Oct. 30 | 4 p.m.-12 a.m. | Tin Roof | $12.50+ | Join the crawl for 2 free drinks at 5+ venues, plus a $1,000 costume contest. 🍻
• Pumpkin Jamboree | Sat., Oct. 30 | 10 a.m.-5 p.m. | Eckert’s Orchard | $5 | Live entertainment, festival food, wagon + camel rides, and fun for kids of all ages. 🎃
• Adult Halloween Costume Party | Sat., Oct. 30 | 7-11 p.m. | Lexington Polo Club | Registration Required | LPC’s first Adult Halloween Costume Party — spooky snacks, costume contest + guests are encouraged to bring brews to share.
• Fresh Food Adventures Dinner | Sat., Oct. 30 | 6:30 p.m. | Shaker Village | $89 | 4-course dinner fun + educational dinner showcasing 9 different preservation techniques.
• Julietta Market Fall Festival | Sat., Oct. 30 | 12-7 p.m. | Greyline Station | Trick-or-treating, music, games + prizes
• Booktacular | Sat., Oct. 30 | 7 p.m. | Virtual | $25 | A virtual James Bond-themed fundraiser to benefit the Lexington Public Library
• Pivot Brewing Halloween and Anniversary Party | Sat., Oct. 30 | 1-8 p.m. | Pivot Brewing | Free | New cider + beer releases, costume contests, Halloween movies, and brewery tours.

Sunday, Oct. 31

• Halloween Ball | Sun., Oct. 31 | 10 p.m. | Madison Garden Bar and Grill, Richmond, KY | Free | A Halloween party at a local Richmond pub featuring DJ Big D. 👻
• Sunday Tunes in the Vines - The Twiggenburys | Sun., Oct. 31 | 2 p.m. | Equus Run Vineyards | Free | Wine, friends + local music will be featured at this family-friendly event. 🍷
• Pumpkin Jamboree | Sun., Oct. 31 | 10 a.m.-5 p.m. | Eckert’s Orchard | $5 | Live entertainment, festival food, wagon + camel rides, and fun for kids of all ages. 🎃