Festivals, Fairs, and Fall Fun: Your Guide to Sarasota’s Most Spooktacular Events

October 2024—Whether you’re hunting for a haunted trail, picking out a perfect pumpkin, or just searching for something safe and spooky to do with your little monsters, there’s something for everyone this fall season! 

Weekends Starting October 5
Annual Pumpkin Fest

Several fall activities including face and pumpkin painting, costume contests, train and hay rides, petting zoo, carnival games and performances by the Torres Family Circus.
Fruitville Grove | fruitvillegrovefarm.com

Weekends Starting October 5
Harvest Festival at Dakin Dairy

Guests will enjoy a cornmaze, Hayrides, games, lawn mower racing, and equipment viewing.
Dakin Dairy Farms | dakindairyfarms.com

October 5
All Faiths Autumn Harvest Dinner

Part of All Faith Food Bank’s fall harvest campaign, this event raises funds for programs that provide fresh fruit and vegetables to people struggling with hunger. 
All Faiths Food Bank Warehouse | allfaithsfoodbank.org

October 5 
Sharktoberfest & Craft Beer Festival

Mote’s annual craft beer festival features local and regional breweries offering samples of their staple selections alongside unique, seasonal brews.
Mote Marine | mote.org

October 5 
Pop’s-Toberfest

The 3rd annual Oktoberfest Celebration in the Pop’s Sunset Grill Beer Garden features festive entertainment by Fred Reimer, Oktoberfest inspired food specials, and a great selection of traditional and local Oktoberfest style beer. Wear your best lederhosen and dirndl for the best dressed competition.
Pop’s Sunset Grill | www.facebook.com/events

October 6 
Park-Tober Fest at The Bay

Celebrate Oktoberfest – The Bay style! Kick off October with a hoppy twist. Make sure to be a part of the world-famous “Chicken Dance” tradition, enjoy the Steinhoisting contest, or a game of cornhole.
The Bay | eventbrite.com

October 9 – 31 
Lights at Spooky Point

Lights at Spooky Point is back with an array of spooky creatures and seasonal lighting along a path through the woods. Refreshments available for purchase.
Historic Spanish Point | selby.org

October 11
Witches Night Out

From 6pm to 10pm at the Historic Edson Keith Mansion in Phillippi Estate Park, guests (witches and wizards) will enjoy music, dancing, shopping, food, and drinks. Dress in your favorite witch or wizard attire or you can dress as a muggle. 
Phillippi Estate Park | visitscgov.net

October 11-13 
Sarasota Rocktoberfest

The ultimate fall celebration in downtown Sarasota has live music and performances to keep you rocking all weekend.
JD Hamel Park | paragonfestivals.com

Weekends Starting October 11 
Discover Sarasota’s Boo Mobile

Hop on board for a fun, family-friendly Halloween party on the trolley! Children and parents, join us for a 45-minute magical tour as WitchyPOO goes on a delightfully musical hunt for her dear missing Pumpkin all around downtown Sarasota’s historic landmarks.
Dolly The Trolley | discoversarasotatours.com

Weekends Starting October 12 
Hunsader Farms Pumpkin Festival

Celebrate fall at Hunsader’s with live music and shows, games, hay rides, food, petting zoo, train rides, pumpkins and more.
Hunsader Farms | hunsaderfarms.com

October 17-22
UTC Fall Festival and Carnival

Florida Penguin Productions & The Mall at University Town Center are back again with the 4th Annual Fall Festival & Carnival. This event features Carnival Rides, Pumpkin Patch for Charity, Pet Costume Contest, Trunk or Treat, Live Community Performances, Food Trucks & Beer Truck, Fall Themed Vendors, Selfie Stops, Activities & More!
The Mall at UTC | mallatutc.com/events/fall-festival

October 18
Bigtoberfest at Big Top Brewing

Enjoy German food, drink specialties, fall vendors, kid-friendly games, crafts, and face painting. 
Big Top Brewery at Fruitville Commons | bigtopbrewing.com/events 

October 18
Haunted Trail Carnival at Arlington Park

This spooktacular event promises an evening of games, trick-or-treating, and festive fun for local kids and families.
Arlington Park & Aquatic Complex | eventbrite.com

October 18-19
Oscar Scherer’s Haunted Trail Event

For those who dare, take a walk in the dark along the eerie road with plenty of scare. Make it to the end & Nokomis Volunteer Fire Department will be there to amp up the scare. Plenty of treats on the Trick or Treat Trail with Osprey Nokomis Chamber of Commerce non-profit businesses & local businesses to sweeten the fun. 
Oscar Scherer State Park | halloweenhauntedtrails.com

October 19
Taste of North Port Food & Fall Fest

Food trucks, parade, costume contest and more in the center of downtown North Port.
Center Green | llsnevents.com

October 19 
Spooktacular Halloween-Themed Movie Night at Ed Smith Stadium

Bring the whole family for this fun fall activity on the big screen at Ed Smith Stadium.  
Ed Smith Stadium | mlb.com

October 19 
a-Scare-ium at Mote Marine

Trick or treat at special stations throughout the Aquarium, complete a scavenger hunt to win a prize, enjoy spooky science and educational encounters with the Mote team, experience a live underwater pumpkin carving, and enjoy a coloring table, bounce house, live music, face painting and other A-scare-ium delights!
Mote Marine | mote.org

October 19-20 
St. Armand’s Fall Festival of the Arts

Discover art and inspiration at the St. Armands Fall Festival. Hosted by Paragon Festivals and the Downtown Sarasota Enrichment Association, this event transforms St. Armands Circle Park into an outdoor gallery of unique, handmade artwork by talented artisans from Florida and across the United States.
St. Armands Circle | starmandscircleassoc.com

October 24-27
The Legend of Sleepy Hollow at The Players Studio

Join The Players Studio at the annual Fall Festival leading into that evenings performance of The Legend Of Sleepy Hollow. Includes food trucks, games, prizes, face painting, a photobooth, a bounce house, and more!
St. Armands Circle | starmandscircleassoc.com

October 25
Lakewood Ranch BooFest

Bring your trick-or-treat bag and enjoy the family-friendly fun at this annual Halloween event.
Lakewood Ranch Main Street | lakewoodranch.com

October 25
Boo! at The Bay

Join in the fun of this 3rd Annual Halloween event which includes a not-so-scary evening filled with trick-or-treating, free pumpkin pickings, yard games, a not-really haunted decorated trail, a movie showing of Despicable Me 4, and more.
Common Ground at The Bay Park | eventbrite.com

October 26
Downtown Sarasota’s Halloween Pub Crawl

Pull out your spookiest costumes, grab your ghoulish friends, and prepare for a night of haunted fun. It’s Sarasota County’s most frightfully fantastic pub crawl, where the spirits are high, and the fun never dies!
Joe’s On Main | eventbrite.com

October 26 
Sarasota Farmer’s Market Dog-A-Ween Costume Contest

Dress up your furry friends in their best costumes and bring them down for a fun-filled day that supports Donte’s Den, a local organization dedicated to providing a safe and loving sanctuary for dogs in need. 
Downtown Sarasota | destinationdowntownsarasota.com

October 29 
Nathan Benderson Park Trick or Treat on the Lake

This is a Halloween event designed with the whole family in mind. Get into the spirit of the holiday with family-friendly Halloween favorites set against the gorgeous backdrop of our lake.
Nathan Benderson Park  | nathanbendersonpark.org

October 31 
Downtown Venice Halloween Strut

Enjoy trick-or-treating at participating locations on Tampa Ave West, West Venice Ave, Miami Ave West, and Nokomis Ave. Groove to kid-friendly music with DJ Steve at the Trunk-or-Treat in the Merchants of Venice building parking lot.
Downtown Venice | visitvenicefl.org

October 31
Fright Night on St. Armands Circle

Enjoy decorated store fronts and frightening characters set the stage for the wandering spirits of St. Armands past. Adults and children trick-or-treat throughout the Circle with numerous retailers and restaurants contributing to the Halloween spirit with candy, games, and customized promotions. 
St. Armands Circle | starmandscircleassoc.com