Lucky you. You just found LALtoday’s Plan Ahead, a list of some of the biggest events to plan for that are taking place in and around Lakeland each month.
Take out your calendar, grab your day planner, or text all your friends — these are the top events we recommend heading to this month. Psst: Don’t forget to bookmark this page and come back; we update our guide monthly.
Don’t see anything you like? Check out our full events calendar.
Follow the lederhosen to Oktoberfest events around Polk County.
Photo by @groverootsbrewing
Seasonal events
Oktoberfest | Friday, Oct. 3-Sunday, Oct. 5 | Times vary | Grove Roots Brewery, Winter Haven | Free+ | The brewery becomes a German beer hall for a weekend filled with live polka music, stein hoisting, and Bavarian cuisine.
Mulberry’s Hispanic Heritage Festival | Saturday, Oct. 4 | 10 a.m.-1 p.m. | Spence Park, Mulberry | Free+ | Get your heart pounding with a Zumba class, play loteria, ride a mechanical bull, and read a bilingual story with Mirabel.
Harvest Days | Saturday, Oct. 4-Sunday, Oct. 19 | 10 a.m.-3 p.m. | Keel Farms, Plant City | Free+ | Ring in the fall season with a hay ride, corn maze, pumpkin patch, pie-eating contest, and seasonal drink releases.
The 2025 Swantoberfest | Friday, Oct. 17-Sunday, Oct. 19 | Times vary | Swan Brewing | Free+ | Drink German beers, dance to live music, and indulge in bites by a different food truck each day.
Even pups can get in on the fun this season.
Photo by @shoplakesidevillage
A Night of Thrills & Chills | Friday, Oct. 17 | 6:30-9:30 p.m. | Camp Margaritaville, Auburndale | $20+ | Be thrilled by a Flying Royals trapeze show and chilled by the haunted house experience.
Halloween Bash 2025: Monster Mash | Friday, Oct. 24 | 5-7 p.m. | Lakeside Village | Free | It’ll be a graveyard smash as you follow the candy trail around the shopping center and meet characters on the lawn.
Creepy, Crawly Fall Festival | Saturday, Oct. 25 | 11 a.m.-2 p.m. | Camp Fire Sunshine | Free+ | Bring your costumed crew for train rides, trunk-or-treating, and games galore.
Pooch O Ween: Pet Parade and Costume Contest | Sunday, Oct. 26 | 2-4 p.m. | Lakeside Village | $10 | Strut your stuff alongside your furry friends and enter costume contests to win Woof Gang gift cards.
PAL-oween Party | Sunday, Oct. 26 | 5-8 p.m. | PAL Complex | Free | Trunk-or-treat and brave a haunted house hosted by the Lakeland Police Athletic League.
Markets + shopping
Lakeland Record Fair, Volume VI | Sunday, Oct. 5 | 10 a.m.-4 p.m. | Lake Mirror Auditorium | $5 | Go treasure hunting through stacks of vinyl records, CDs, cassettes, and music memorabilia.
Plant Pop Up | Saturday, Oct. 11 | 8 a.m.-2 p.m. | Munn Park | Price of purchase | Spruce up your garden for fall thanks to the plants + tools sold by local vendors.
Polk State FallFest | Saturday, Oct. 11 | 9 a.m.-3 p.m. | Polk State College, Winter Haven | Price of purchase | More than a hundred vendors and college clubs will set up craft booths and a car show.
Fall Plant Sale & Flower U-Pick | Friday, Oct. 24-Saturday, Oct. 25 | 9 a.m.-2 p.m. | Sow Exotic Nursery, Winter Haven | Price of purchase | Create bouquets and flower crowns out of zinnias, take a photo in the pumpkin patch, and shop for exotic plants.
Fall Night Market | Saturday, Oct. 25 | 5-9 p.m. | Downtown Lakeland | Price of purchase | Dine, groove, and shop down the street with 150+ vendors set up under the stars.
Get active
All Elite Wrestling Collision | Thursday, Oct. 2 | 7:30 p.m. | RP Funding Center | $31+ | Pro wrestlers like Big Bill and Ricochet take to the ring for a televised, action-packed event.
Run for the Boolies | Saturday, Oct. 4 | 6 p.m. | Lake Hollingsworth | $35 | Run, walk, or zombie crawl to the finish line at this dog-friendly 5K benefitting Polk County Bully Project.
Florida Roundnet Lakeland Tournament | Saturday, Oct. 11 | 9 a.m.-5 p.m. | Hunt Fountain Park | $10+ | Polk County Roundnet hosts the fourth stop on the Florida Roundnet Tour Series.
InnerAct Alliance 2025 Red Ribbon Run | Saturday, Oct. 25 | 6 a.m.-1 p.m. | Lake Mirror | Free+ | Families can take a fun run together around the lake and learn about healthy habits at the vendor area.
Fore The Kids Golf Tournament | Monday, Oct. 27 | 10 a.m.-6 p.m. | Cleveland Heights Golf Course | $250+ | Raise money for Boys & Girls Clubs of Polk County by swinging in the longest drive, closest to the pin, and hole-in-one challenges.
Get social + give back
The Plot: Fundraiser for Little Bus Books | Thursday, Oct. 2 | 6 p.m. | Union Hall | $30+ | Little Bus Books is transitioning into a nonprofit called No Covers — join its debut fundraiser with a panel of mystery authors.
Ten Story Challenge | Friday, Oct. 3 | 2-10 p.m. | Lakeland Electric Building | Free+ | Watch Lakelanders rappel down the Lakeland Electric building as you enjoy food trucks and entertainment at the landing site.
5th Annual Rally & Ride Out of the Darkness | Saturday, Oct. 4 | 8 a.m.-3 p.m. | SUN ‘n FUN | $15+ | Join an escorted motorcycle ride from the Auburndale Speedway to a rally at SUN ‘n FUN.
10th Annual Puttin On The Pink Breast Cancer Fundraising Event | Friday, Oct. 10 | 5:30-10 p.m. | Winter Haven Moose Lodge | $40 | Enjoy a prime rib dinner and the Brotherhood of Pinkness Fashion Show at this benefit for the Hollis Cancer Center.
Rainbow Roots Festival | Sunday, Oct. 12 | 12-6 p.m. | Lake Mirror Auditorium | Free | The Rose Dynasty Foundation hosts this family-friendly celebration of LGBTQ+ art, history, music, and more.
Midnight at the Masquerade | Saturday, Oct. 25 | 6-9:45 p.m. | Eala’s Speakeasy | $150+ | Get dressed in your finest evening wear for an interactive murder mystery experience with gourmet bites by Frescos, all in support of ROAR Florida.
Cardboard Boat Challenge participants can choose to pre-build boats or make them on-site at Lake Hollingsworth.
Photo by City of Lakeland
Family fun
Fall Family Festival | Saturday, Oct. 4 | 10 a.m.-2 p.m. | The Ashley Gibson Barnett Museum of Art | Free | Visitors of all ages can get in the fall spirit with family activities like a magic show and a scavenger hunt through the galleries.
20th Annual Cardboard Boat Challenge & Lakes Festival | Saturday, Oct. 11 | 8 a.m.-1 p.m. | Lake Hollingsworth Boat Ramp | Free+ | Boats made of cardboard will sink or sail as spectators enjoy music from the Sofa Kings’ party barge.
Circus Royale Class | Saturday, Oct. 11-Saturday, Oct. 18 | Times vary | Camp Margaritaville, Auburndale | $45+ | Kids and adults can discover their inner big-top performers with hands-on trapeze lessons.
Lake Mirror Classic Concours and Car Show | Friday, Oct. 17-Sunday, Oct. 19 | Times vary | Frances Langford Promenade | Free | Join the Hot Rod Rendezvous on Friday, the Concours d’Elegance on Saturday, and the Lake Mirror Classic Road Tour on Sunday.
A Teen Masquerade Fantasy Ball | Friday, Oct. 24 | 7:30-10 p.m. | Peggy Brown Building | $35 | Masks and costumes are required for this dance hosted by local author Sofia Simpson.
Food + drink
Taste of Lakeland | Saturday, Oct. 4 | 10 a.m.-5 p.m. | Apostle Henry Ross Family Life Center | Price of purchase | Enjoy mouthwatering dishes from a variety of food trucks and restaurants, plus cultural performances.
Wine Dinner | Thursday, Oct. 9 | Times vary | Garden Bistro | $75 | Indulge in a five-course meal with wine pairings and a live classical guitar soundtrack.
Central Florida Food Fest | Saturday, Oct. 18 | 5-9 p.m. | Bonnet Springs Park | $15 | Indulge in exclusive food and drinks from local restaurants, live music, and an artisan market.
Cauldron Crawl | Saturday, Oct. 18 | 6 p.m. | Downtown Lakeland | Price of purchase | Sip your way to Molly’s, Chop Shop, Mojo Federal, Linksters, and Smith’s American Tavern on this wickedly fun bar crawl.
Head to the Silver Moon for exclusive movie events this month.
Photo by @honey.allison
Pop culture + film
Girl Dinner: Taylor Swift Album Release Party | Friday, Oct. 3 | 6-9 p.m. | Bonnet Springs Park | $5 | Celebrate the release of Taylor Swift’s new album with cocktails, crafts, small bites, and a DJ at the Rooftop Bar.
Taylor Swift: “The Official Release Party of a Showgirl” | Friday, Oct. 3-Sunday, Oct. 5 | 7 p.m. | Silver Moon Drive-In | $12.50 | Pile into your car for Polk County’s only drive-in screening of this event.
Taylor Swift Album & Engagement Skate | Friday, Oct. 3 | 7-10 p.m. | Skate World Lakeland | $10+ | Dress up to skate through the eras along with other Swifties.
The Rocky Horror Drive In 50th Anniversary Kick Off Spectacular | Saturday, Oct. 4 | 11:30 p.m. | Silver Moon Drive-In | $25 | Arrive early to grab a seat on the lawn to do the Time Warp with the cast of Hell on Heels Tampa.
Lakeland Horror Film Festival | Saturday, Oct. 25 | 9 a.m.-11:55 p.m. | CMX Lakeside Village 18 & IMAX | $15+ | Watch 27 independent films from around the world and see which ones win the “Oscares” awards.
Arts + theater
“Love Quest” | Wednesday, Oct. 1-Sunday, Oct. 26 | Times vary | Theatre Winter Haven | $45 | Patrick Duffy (“Dallas”) and Linda Purl (“Happy Days”) join forces for a romantic play about the world of online dating.
The Last Note | Thursday, Oct. 2 | 6-8 p.m. | The Ashley Gibson Barnett Museum of Art | Free | Send off the exhibition “Above All, Enjoy The Music: Photographs by Herman Leonard” with a performance by the Swan City Jazz Project.
“Frozen” | Thursday, Oct. 2-Saturday, Oct. 4 | 7:30 p.m. | Theatre Winter Haven | $39 | “Let it go” at this stage performance of the beloved Disney musical phenomenon.
Australia’s Thunder from Down Under | Saturday, Oct. 25 | 7:30 p.m. | Polk Theatre | $45+ | Things will get wild at this stop on the male revue’s “Temptation Tour.”
Music
Boots and Boos Line Dancing Night | Saturday, Oct. 4 | 6:30-10 p.m. | Camp Margaritaville, Auburndale | $5+ | Dust off your boots and a Halloween costume for a spirited night on the dance floor.
Classic Albums Live: Bon Jovi - “Slippery When Wet” | Friday, Oct. 10 | 6:30 p.m. | RP Funding Center | $40+ | “Let It Rock” and “Raise Your Hands” at this rocking show featuring every song from Bon Jovi’s hit album.
Lakeland Symphony Orchestra Concert: Monuments in Sound | Saturday, Oct. 11 | 7-8:30 p.m. | Branscomb Auditorium at Florida Southern College | $30 | Guest conductor Robert Moody will lead the orchestra in Barber’s Adagio for Strings and Mahler’s Symphony No. 1 “Titan.”
Candlelight: A Haunted Evening of Halloween Classics | Sunday, Oct. 26 | 2:30-3:45 p.m. | Lake Mirror Auditorium | $36+ | The Listeso String Quartet will string you along for renditions of songs like “Thriller” and “Night on Bald Mountain.”
Have an event of your own you want to share with us? Follow these easy steps to add your events to our calendar:
- Go to our Events page.
- Click “Add Event” in the top right-hand corner.
- Make sure to include a link and fill out important information like the date, time, location, and price of your event.
- Click “Submit,” and you’ve just added an event to our website calendar.