Search Sarasota Real Estate on
Contact us: 888-552-5228

18 October Events and Festivals in Sarasota, Manatee & Charlotte Counties

By: | | Share Tweet Email

Perhaps you’ve felt it? A fresh wind from the north signifying the end of summer. As the warmer months melt into fall, our region is abuzz with festivals and fun happenings. Here’s a list of some of our favorites. See if you can make it to all of them!

Pumpkin Festivals

Hunsader Farms 26th Annual Pumpkin Festival near the Lakewood Ranch area: October 13-14, 28-29

29th Annual Fruitville Grove Pumpkin Fest in East Sarasota: October 7-8, 14-15, 21-22, 28-29

Fall Festivals & Events

Clydesdales: October 13
Set your eyes on the world famous Budweiser Clydesdale Horses in downtown Sarasota between First and Main Street. 4pm-8pm.

32nd Annual Concours d’Elegance: October 14
Suncoast Jaguar Club of Florida is hosting this car-lovers dream on St. Armands Circle showcasing vintage through modern Jaguar cars. 9am-5pm

2017 Florida International Air Show: October 14-15
Aviation enthusiasts will love this weekend event held at the Punta Gorda Airport featuring Kid Zone, helicopter rides, aerobatic performances, military jets, Friday night fireworks and more. Learn more at

Ringling International Arts Festival: October 18 – 21
Join artists and audiences from around the globe for four days of contemporary music, theatre, and dance. For more information and to purchase tickets, view The Ringling website.

Annual Sun Fiesta: October 20 – 22
Enjoy arts and crafts, funny bed races, a parade and the Miss Sun Fiesta Pageant in downtown Venice. Learn more at the Women’s Sertoma Club of Venice.

Bayfest on Anna Maria Island: October 21
Anna Maria Island is hosting one of its most popular annual music, food, arts, and crafts festivals October 21th from 10am – 10pm. Taking place on Pine Avenue, get the full scoop on the Anna Maria Chamber of Commerce website.

Fall Extravaganza in Port Charlotte: October 28
Held on the Charlotte County Fairgrounds, crafts, games, music, hayrides, food, and entertainment will provide family-friend fun for free from 10am – 5pm.

War on the Peace Dragon Boat Festival: October 28
Celebrate Halloween at Punta Gorda’s War on the Peace Dragon Boat Festival, which will be held on the Peace River waterfront at Laishley Park! Learn more at

23rd Annual Downtown Sarasota Arts & Craft Festival: October 28-29
Head to Main Street in downtown Sarasota for contemporary crafts from more than 100 artisans. Enjoy free admission from 10am – 5pm.

Halloween Events

Hall-O-Ween Movie Night Spooktacular: October 14
Head to Ed Smith Stadium to enjoy a movie, games, and a Halloween costume parade. 5pm – 8pm

Night of Fun, Fish, and Fright at Mote Aquarium: October 20
The kids will enjoy dressing up, mad science experiments, and live shows at this favorite Halloween event held at Mote.  6pm-8:30pm.

Boo Fest Halloween Festival at Lakewood Ranch: October 27
Main Street, Lakewood Ranch is hosting the 12th annual Boo Fest featuring trick or treating, the Spooktacular Maze, music and more. Dress in costume! Learn more. 6pm-9pm.

Haunting on the Harbor: October 27-31
The 8th annual Haunting on the Harbor Halloween Festival & Haunted House returns to downtown Punta Gorda. 6,000 sq. ft. Haunted House, the largest in SW Florida! Lashley Park. Find out all the details on their Facebook page.

9th Annual Fright Night on St. Armands Circle: October 31
Haunted storefronts, frightening characters and trick or treating will bring everyone to Sarasota’s favorite circle. Stay for the performance of Thriller at 8pm. 6pm-8:30pm

22nd Annual Dearborn Street Halloween Safe Walk: October 31
Trick-or-treat on Dearborn Street in Englewood featuring live music, pet costume contest, and ghoulish goodies and treats. Learn more.


Are there more spectacular and spooktacular events we missed? Comment below to let everyone know!

18 October Events and Festivals in Sarasota, Manatee & Charlotte Counties was last modified: October 10th, 2017 by Kathryn Parks