🎃 Fall & Halloween Fun in Sarasota: The Best Events This October 2025
October in Sarasota means cooler nights, pumpkin spice everything, and a calendar packed with fall festivals, Oktoberfest celebrations, and spooky Halloween thrills. Whether you’re hunting for the perfect pumpkin, rocking out at a downtown festival, or trick-or-treating with the kids, Sarasota and nearby Bradenton and Venice have plenty of seasonal fun to keep you busy. Here’s your ultimate guide to October’s can’t-miss events.
October 1: Phillippi Farmhouse Market
The wait is over! Sarasota’s favorite outdoor market is back. Stroll the open-air stalls for fresh produce, baked goods, flowers, handmade crafts, and live music. Free entry every Wednesday from 9 a.m. – 2 p.m. at 5500 S. Tamiami Trail, Sarasota.
October 1 – 26: Edelweiss Oktoberfest in Bradenton
Raise a stein at Edelweiss’ 13th Annual Oktoberfest! Enjoy authentic German food, a huge beer tent, live music, and Saturday costume contests. Open daily noon – 8 p.m. at 611 Manatee Ave E, Bradenton. Admission is free.
October 3 – November 1: Lights at Spooky Point
Historic Spanish Point gets a Halloween glow-up! Wander through glowing trails, whimsical displays, and magical light shows. A family favorite that’s more enchanting than scary. Tickets from $19 kids / $34 adults at 401 N. Tamiami Trail, Osprey.
October 4: Wellen Park Oktoberfest
Bust out your lederhosen! Wellen Park’s Oktoberfest is back with German dancers, live polka, a stein-hoisting contest, and Bavarian eats. Runs noon – 8 p.m. at 19745 Wellen Park Blvd, Venice.
October Weekends: Fruitville Grove Pumpkin Fest
This Sarasota classic is now in its 37th year! Pick pumpkins, hop on hayrides, enjoy pony rides, live shows, and even a haunted manor for the brave (ages 8+). Admission and parking are free; activities $1–$10. Open weekends Oct. 4–5, 11–12, 18–19, 25–26, 10 a.m. – 5 p.m. at 7410 Fruitville Rd.
October 10: Witches Night Out
Calling all witches and wizards! Dress up for a magical evening at the historic Edson Keith Mansion with a DJ, costume contest, shopping, and food & drinks. Tickets $35. Runs 6 – 10 p.m. at Phillippi Estate Park, Sarasota.
October 10–11: Symphonic Spooktacular in Venice
Get goosebumps in the best way with The Venice Symphony’s season opener. Hear chilling classics like Psycho and The Sorcerer’s Apprentice at the Venice Performing Arts Center.
October 11: Oktoberfest – A Day of Oars & Pours at Nathan Benderson Park
Rowing + Oktoberfest = fall fun, Sarasota-style! Enjoy the Benderson Chase regatta alongside music, dancing, food, and plenty of cold beer. Free event, 10 a.m. – 4 p.m. at 5851 Nathan Benderson Circle. Parking $20.
October 11–12, 18–19, 25–26: Hunsader Farms Pumpkin Festival
A fall tradition you can’t miss. Live music, a craft show, hayrides, pioneer village, and endless pumpkin fun. Admission $15 adults, $5 kids (ages 5–9), under 5 free. Parking $5, cash only. Open 9 a.m. – 5 p.m.
October 17: Goblin Gathering at GT Bray Park
Bring the family for trick-or-treating, bounce houses, a petting zoo, and costume contests at this free event. 4 – 8 p.m. at 5502 33rd Ave Dr W, Bradenton.
October 17–19: SRQ Rocktoberfest
Downtown Sarasota comes alive with live music, craft vendors, delicious food, and seasonal brews. Free entry at J.D. Hamel Park all weekend long.
October 18: Boo! at The Bay
A family favorite returns! Trick-or-treating, pumpkin decorating, games, a decorated trail, and an outdoor movie under the stars. Free event, 6 – 8:45 p.m. at The Bay Park.
October 23–25: Legend of Sleepy Hollow at Sarasota Polo Club
Don’t lose your head! The Players Centre brings Ichabod Crane and the Headless Horseman to life in this outdoor production. Wear a costume for the nightly contest. Tickets $15–$30, show at 6 p.m. at 8201 Polo Club Ln.
October 24: BooFest at Lakewood Ranch
Main Street transforms into a spooky carnival with inflatables, live shows, trick-or-treating, and free pumpkin totes for the first 1,500 kids. Runs 6 – 9 p.m.
October 25: Halloween Fun All Day
Boo Run 5K: Start the day with a costumed run at 8 a.m.
Bradenton Public Market: Trick-or-treat 9 a.m. – 2 p.m. on Old Main St.
Dog-A-Ween: Adorable pup parade + costume contest at 10 a.m. in Paul Thorpe Park.
October 28: Trick-or-Treat on the Lake at Nathan Benderson Park
Follow a decorated candy trail, enjoy live music, storytelling, and activities for the kids. Free event, 5:30 – 8 p.m. on Regatta Island.
October 31: Halloween Night Happenings
Siesta Key Safe Treats: A 40-year tradition with free trolley rides, 3 – 6 p.m.
Venice Halloween Strut: Downtown trick-or-treating, 4:30 – 6:30 p.m.
Halloween at The Ringling: Trick-or-treating, art, and galleries, 4:30 – 7:30 p.m. Free.
Fright Night on St. Armands Circle: Haunted storefronts + family fun, 6 – 8:30 p.m.
October 31 – November 2: Sarasota Fall Festival & Carnival at UTC
Close out the season with carnival rides, food trucks, live shows, and trunk-or-treat. Festival hours Sat–Sun 11 a.m. – 6 p.m., Carnival opens Fri at 5 p.m. at the Mall at UTC.
🍂 Your Sarasota October Guide
From pumpkin patches and Oktoberfest to glowing trails and spooky parades, Sarasota has something festive happening almost every day this October. Grab your costume, mark your calendar, and get ready for a month packed with fall fun and Halloween magic!
