Pumpkin Fest
Siesta Key Crystal Classic
Medieval Fair - Photo Courtesy of the Sarasota Medieval Fair.

Fall Activities for the Whole Family in Sarasota

School is back in session and the summer heat and humidity have begun to make their retreat... it must be fall in Sarasota!

In October, enjoy the autumnal season with the whole family by hitting up the pumpkin patch or find the best Floridian trick or treat haunts—on the beach, among the palm trees, and even under the sea.

As the season continues, indulge in the crisp fall weather with outdoor music, art festivals, nature-themed events and more throughout the entire autumn in Sarasota County.


Pumpkin Festivals

Great news for anyone who appreciates a good gourd: There's a pumpkin festival for every weekend of the month in Sarasota! Pick out the perfect pumpkins to carve Halloween Jack 'O' Lanterns, go on a hayride, play carnival games and chow down on harvest-season fair foods at Sarasota's family-friendly pumpkin festivals.

Trick-or-Treat and Halloween Themed Family Events

Halloween season brings out Sarasota's best selection of things that go bump in the night and not-too-spooky frights that are sure to delight the whole family. Suit up in your best Halloween costume and hit up a community trick or treat event—the candy is calling!

  • October 14: All ages are welcome to enjoy a movie and games at the 3rd annual Howl-O-Ween Movie Night Spectacular at Ed Smith Stadium—but please keep in mind, no strollers or high heels on the field.
  • October 20: Mote Marine's annual Night of Fish, Fun, and Fright invites "buoys and ghouls" of all ages to participate in a spooky sea-themed Halloween filled with sweets treats, underwater pumpkin carving, and shark's teeth-hunting in "Coffin Creek."
  • October 20 - 21: Hit the Haunted Trails at Oscar Scherer State Park. The Trick or Treat Trail is for the wee ones, while the Scary Trail and Haunted House will appeal to the brave of heart.
  • October 27: Lakewood Ranch BOO Fest takes over LWR Main Street with a 'Spooktacular Maze,' Halloween dancers, balloon artists, and an abundance of trick-or-treat candy.
  • October 27 & 28: The Players Centre for Performing Arts presents "The Legend of Sleepy Hollow," a theatre in the field experience. The show takes place at the Sarasota Polo Grounds at 6 p.m.  Possible rain delay Oct. 29.
  • October 29: Selby Gardens Spooktacular is a daytime Halloween event for the whole family that features pumpkin decorating, trick or treating, 'mad botanist' science experiments, and seed planting.
  • October 31: For a breezy and beachy all Hallows Eve, trick or treat at the annual Siesta Key Village Safe Treats for Kids. The Siesta Key Chamber of Commerce and participating businesses will hand out candy in costume throughout the Village from 3:00 p.m. - 6:00 p.m. on Halloween.
  • October 31: Circumambulatory trick or treating is all the rage at Fright Night on St. Armands. Join the wandering spirits of St. Armands past as you tour the Circle for treats. Don't miss the traditional performance of "Thriller" in collaboration with the Sarasota High Drama Department at 8:00 p.m..
  • October 25: The Humane Society of Sarasota County presents its 20th annual Howl-O-Ween Pet Costume Contest at the Phillippi Creek Farmers Market. Contest categories include funniest, spookiest, most creative, best pet/owner look-a-like, and best costumed rescues.
  • October 27: Don't miss Trick or Treat at City Hall in North Port (4970 City Hall Blvd.) This signature event is an evening of free, family-friendly trick or treating that transforms the three floors of City Hall into magical scenes with Halloween goodies.
  • October 31: Venice Main Street holds its Halloween Parade 4 p.m. in downtown Venice

Other October Attractions

  • Weekly Wednesdays: It's market season, once again, at the Phillippi Farmers Market! The season re-opening takes place on October 4, with market hours every Wednesday from 9:00 a.m. - 2:00 p.m. through April.
  • October 8-9: Ring in the soups 'n' stews season with the Sarasota Firemen's Benevolent Fund 18th annual Morton's Firehouse Chili Cook Off to see whose chili reigns supreme among 15 competing firehouses from Sarasota, Englewood, North Port and Boca Grande.
  • October 14: Join the Master Gardeners Chapter of the Friends of Sarasota County Parks in their free, family-friendly Annual Plant Sale featuring sustainable gardening education, landscape problem diagnosis, and thousands of plants for sale.
  • October 14-15: The 11th annual Sarasota Magyar Festival celebrates Hungarian culture with traditional dance, food, European beer, archery demonstrations, arts and crafts, and more. Kids can enjoy the bounce house, pony rides, and 'Kids Corner' programs.
  • October 21: Need a bagpipe fix or an excuse to wear your kilt? The Sarasota Celtic Music Festival brings Celtic rock, folk, and fusion music to the Sarasota stage.
  • October 21: The family friendly Sarasota PrideFest celebrates Sarasota's LGBT+ community and supports equality for all. Enjoy live music, connect with local LGBT organizations, shop the vendors, and picnic on the lawn at J.D. Hamel Park.
  • October 27-28: The 21st annual Giving Hunger the Blues Festival takes place rain or shine, on October 28 from 11:30 a.m. - 9:30 p.m. on the lawn of the iconic Van Wezel. GHTB Fest weekend kicks off with "Giving Hunger the Boos" on October 27 with Reverend Barry & Funktastic Soul, featuring the Hellacious Horns.


  • November 4: Celebrate the great outdoors with the Conservation Foundation's Wild About Nature Festival. Climb trees, participate in conservation activities, take hula hoop lessons, get your face painted and practice kayaking at this free event at Bay Preserve in Osprey.
  • November 4-5: Bring the whole family for the Beer, Boats and Bacon Festival at Nathan Benderson Park. This year's festival features live music, over 80 craft beers to sample, bacon-centric dishes from local chefs and restaurants, and a family-friendly 'learn to row' area.
  • November 4-5, 11-12, 18-19: Munch on a roasted turkey leg while you enjoy jousting, human combat chess, medieval-themed comedy acts, Highland bagpipes, aerial shows, the artisan marketplace, and more at the Sarasota Medieval Fair.
  • November 10-13: Celebrate the 10-year anniversary of the Sarasota Chalk Festival at the Venice Airport Festival Grounds. Experience Chalk Fest favorites like the Pavement Music Festival and the real-time creation of awe-inspiring 3D works by street artists from across the globe. New to this year's festival: the opportunity to view the work from above in hot air balloon rides!
  • November 10-13: Sand sculptors from across the U.S. gather for the Siesta Key Crystal Classic, where they transform the powdery white sands of Siesta Key into magnificent, marble-white statues on the beach. Enjoy the art—or try your own hand in the sand during the amateur sculpting competitions.
  • November 12: Kick off the giving season with Bowls of Hope at Ed Smith Stadium. Each guest selects a beautiful handcrafted bowl donated by local artists to enjoy soup, bread and desserts from 40 local restaurants. Proceeds support All Faiths Food Bank.
  • November 18: The annual Venice Blues Festival will take place at Maxine Barritt Park, featuring the blues and grooves of CeCe Teneal, Tommy Z, Eliza Neals, Andrew 'Jr. Boy' Jones, and Elvin Bishop.

Fall in Love with Sarasota

The winter holidays are right around the corner, but make sure to take time to stop and smell the pumpkin spice in Sarasota this fall.

Family-friendly events throughout the season offer a wholesome schedule filled with tricks and treats, knights in shining armor, bacon and beer and boats, chalk art masterpieces, and plenty of pumpkins: there's something in Sarasota's autumn air for everyone to enjoy!