Sarasota families do not need to wait until Halloween night to find pumpkins, costumes and a reason to get together this October.

From farm hayrides to a waterfront celebration, the coming weekends offer several different ways to enjoy the season, with a neighborhood chili fundraiser adding another option for Sunday afternoon.

Fruitville Grove: pumpkins and hayrides

Fruitville Grove’s 2026 Pumpkin Festival runs on October 10–11, 17–18, 24–25 and October 31–November 1, following its opening weekend earlier this month.

Festival hours are 10 a.m. to 5 p.m. on Saturdays and Sundays, with $5 admission, free entry for children six and younger, and free parking.

Hayrides, pumpkin painting, pony rides and a haunted house are among the advertised activities, but individual attractions have separate prices.

That distinction matters when planning a family budget: admission does not mean every activity is included.

The farm also lists free entertainment and a Saturday children’s costume contest at 2 p.m.

Bring cash for vendors and check the organizer’s current information before heading out.

Hunsader Farms: a nearby farm outing

Families willing to travel beyond Sarasota can visit Hunsader Farms at 5500 County Road 675 in Bradenton.

Its pumpkin festival runs October 10–11, 17–18 and 24–25 from 9 a.m. to 5 p.m.

Advertised attractions include hayrides, pumpkins, live music, a petting zoo and a corn maze, with some activities priced separately.

Admission is $15 for ages 10 and older, $5 for children ages five through nine, and free for children younger than five.

Parking costs $5, and festival admission and parking are cash only.

Boo! at The Bay: a free Sarasota celebration

Boo! at The Bay is scheduled for Saturday, October 17, from 5 to 7:45 p.m. at Common Ground, 1055 Boulevard of the Arts.

Families can enjoy trick-or-treating, yard games and free pumpkin picking and decorating, with pumpkins available to the first 1,800 children.

The evening includes a sing-along screening of The Nightmare Before Christmas beginning at 6:30 p.m.

Bring a lawn chair or blanket, and budget separately for food-truck purchases.

If weather forces postponement, the organizer lists October 24 as the alternate date.

Morton’s: chili with a community purpose

The 26th Annual Morton’s Firehouse Chili Cook-Off takes place Sunday, October 11, outside Morton’s Gourmet Market at 1924 South Osprey Avenue.

The main event is advertised for 2–5 p.m., while its event listing begins at 1:45 p.m., so arriving a little early is a sensible option.

Firehouse teams compete over chili and booth presentation, with proceeds benefiting the Sarasota Fire Fighter’s Benevolent Fund.

The fund supports firefighters and their families during crises.

A visitor-guide listing gives free admission and a $15 chili-sampling fee; confirm tasting arrangements with the organizer.

The cook-off is an October community outing rather than a Halloween event, but it belongs on the same weekend-planning calendar.

Plan the outing that fits your family

Choose the farm festivals for pumpkins and rides, The Bay for a free costume-friendly evening, or Morton’s for food and a charitable neighborhood gathering.

Check the linked organizers for updates, activity prices and weather changes before leaving home.

Details were checked October 5, 2026.