Halloween on Anna Maria Island

Celebrate Halloween Anna Maria Island-Style

October on Anna Maria Island is a special kind of magic. The Gulf waters are still warm, the beaches are peaceful, and the island’s tight-knit community comes alive with festive, family-friendly Halloween fun. Fall is known as the “quiet season” here, i.e. fewer crowds, easy parking, and just the right mix of sunshine and sea breeze. It’s the perfect time to plan a relaxing coastal getaway with a splash of spooky charm.

Whether you’re visiting for a weekend or spending fall break on the island, here are some of the best ways to celebrate Halloween across Anna Maria, Holmes Beach, and Bradenton Beach - plus a few favorite family festivals just over the bridge.

👻 Trail of Treats

Friday, October 31, 2025 | 4 PM – 6:30 PM

Kick off your Halloween with one of Anna Maria Island’s most beloved traditions! The Trail of Treats, hosted by the Anna Maria Island Chamber of Commerce, begins with a children’s costume contest at 4:00 PM. After the contest judging, little ghouls and goblins hit the streets to trick-or-treat at participating island businesses in Holmes Beach. This event is safe, walkable, and full of small-town spirit - think candy, costumes, and friendly shop owners who go all out with decorations. Pick up your event map from the Chamber office at 5313 Gulf Drive in Holmes Beach.

🍭 Trick-or-Treating Hot Spots

Pine Avenue (Anna Maria):

This charming main street transforms into a storybook Halloween setting, with boutiques and cafés handing out treats and decorating their windows. The walkable layout and festive vibe make it perfect for families with younger kids.

Bridge Street (Bradenton Beach):

On the south end of the island, Bridge Street joins the fun with candy stops, costumed shopkeepers, and waterfront views. Stroll the pier at sunset for the ultimate Halloween photo op.

🎃 Hunsader Farms Pumpkin Festival

Weekends in October | 9:00 AM – 5:00 PM

If you’re up for a short country drive east of Anna Maria Island to Bradenton, Hunsader Farms hosts one of the area’s biggest fall festivals. Expect classic fun: a pumpkin patch, hayrides, craft vendors, live music, a petting zoo, and delicious seasonal treats (don’t miss the fried green tomatoes or pumpkin pie!). It’s an ideal outing for families who want a full fall experience under the Florida sunshine.

🧛 Goblin Gathering at GT Bray Park

Friday, October 17, 2025 | 4:00 PM – 8:00 PM

This free event in Bradenton is packed with family entertainment - costume contests, bounce houses, trick-or-treat booths, and food vendors. It’s a great pre-Halloween celebration and a wonderful choice for younger kids who can’t wait until the 31st to dress up.

🏝️ Plan Your Halloween Getaway

From pumpkin festivals to beachside trick-or-treating, Anna Maria Island delivers a safe and spirited Halloween that families will remember for years to come. Whether you stay in Anna Maria, Holmes Beach, or Bradenton Beach, you’ll find that fall brings the perfect blend of island calm and festive fun.

At Beach Boutique Rentals, our family-friendly vacation homes keep you close to the excitement - and even closer to the sand. After a full day of candy collecting and costumed fun, unwind by your private pool, fire up the grill, and enjoy the cool Gulf breeze under the stars.

Ready to make this Halloween your most memorable yet? Explore our Anna Maria Island vacation homes and start planning your fall getaway today!