Halloween on Anna Maria Island is all about family fun, community spirit, and a touch of island charm. Fall is considered the island’s “slow season,” which means fewer crowds, cooler breezes, and an even more relaxed pace. Making it one of the best times to visit our special island. Whether you’re traveling with little ones ready to trick-or-treat or searching for adult-friendly festivities, you’ll find safe and exciting ways to celebrate across Anna Maria, Holmes Beach, and Bradenton Beach. Even just a short drive away, Bradenton and Lakewood Ranch host lively fall festivals and spooky celebrations of their own, that gives you endless ways to enjoy the season. Here’s your 2025 guide to the best Halloween happenings on Florida’s Gulf Coast!
Family-Friendly Halloween Events
Trail of Treats – October 31, 2025, | 3:30 PM – 7:00 PM
One of the island’s most beloved traditions! Hosted by the Anna Maria Island Chamber of Commerce, the fun kicks off at 3:30 PM with a kid’s costume contest at the Center of Anna Maria Island. At 4:00 PM, families head out to trick-or-treat at participating local businesses across Anna Maria, Holmes Beach, and Bradenton Beach. The night wraps up at 7:00 PM, giving families plenty of time to enjoy a safe, walkable Halloween filled with candy, costumes, and community spirit from our little island!
Trail of Treats - Anna Maria Island Chamber of Commerce
Pine Avenue Trick-or-Treating – October 31, 2025, | Evening
Stroll down Pine Avenue in the City of Anna Maria, where charming boutiques and shops decorate their storefronts and hand out treats to excited trick-or-treaters. The walkable, small-town feel makes it one of the coziest and safest spots to enjoy Halloween with kids.
Bridge Street Trick-or-Treating – October 31, 2025, | Evening
Just like Pine Avenue, Bridge Street in Bradenton Beach transforms into a festive Halloween destination. Shops and restaurants along the street welcome families for candy, photos, and plenty of spooky fun in a relaxed, island-style setting!
Holmes Beach Neighborhood Trick-or-Treat – October 31, 2025, | Evening
For those who love a more traditional Halloween, Holmes Beach neighborhoods come alive with decorations and community spirit. Residents often go all out with creative displays, making it a fun, safe spot for kids to knock on doors and fill their treat bags.
Goblin Gathering at GT Bray Park – October 17, 2025, | 4:00 PM – 8:00 PM
Head into Bradenton for this free family event filled with bounce houses, face painting, games, and a lively costume contest. Trick-or-treating booths and food vendors make it an easy evening outing for families looking for a safe pre-Halloween celebration.
Goblin Gathering
BooFest on Main Street – October 24, 2025, | 6:00 PM – 9:00 PM
Main Street in Lakewood Ranch comes alive with trick-or-treat booths, inflatables, balloon twisters, and live entertainment on the main stage. This popular event offers a safe, well-organized night out for families, with something to entertain kids of all ages!
BooFest on Main Street – Lakewood Ranch
Hunsader Farms Pumpkin Festival – Weekends in October 2025 | 9:00 AM – 5:00 PM
A Bradenton fall classic! Families can enjoy pumpkin patches, hayrides, a corn maze, craft vendors, live music, and more. It’s the perfect way to embrace the season beyond Halloween night and capture all those festive fall photos.
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Halloween Fun for Adults
Haunted Run – October 25, 2025 | Daytime
This spirited race gives runners a chance to celebrate Halloween in costume while enjoying a fun, active event. Whether you’re racing for time or just out for the spooky vibes, it’s a unique way to mark the season.
Haunted 5K, 10K, 13.1 & 26.2 at Heritage Harbor Park, Bradenton, FL (43) 150
Florida Beach Horses Witch Ride – October 25, 2025 | Evening
For a truly enchanting and equine-inspired, twist on Halloween; saddle up for the Witch Ride hosted by Florida Beach Horses. This unique horseback “cruise ride” offers a magical evening where witches (and wizards!) parade in costume along the shoreline. Tickets are limited, and there are no online bookings, call to reserve your spot!
Florida Beach Horses Witch Ride
Spooky Sunset Cruise – October 31, 2025, | Evening
Swap sidewalks for Gulf waters with a festive sunset cruise. Many local charters offer themed cruises around Halloween, where you can dress in costume, sip seasonal cocktails, and soak in the golden island sunset.
Costume Parties & Themed Cocktails – Late October 2025
Local restaurants and bars often host Halloween parties with prizes for the best costumes, live music, and specialty drinks. It’s a perfect option for couples or groups of friends looking to extend the celebration into the night.
Tips for a Safe & Fun Halloween
- Confirm event dates and times before heading out.
- Use the Trail of Treats map from the AMI Chamber of Commerce to find participating stops.
- Stick to walkable areas like Pine Avenue and Bridge Street for stress-free trick-or-treating.
- Bring water and comfy shoes. October evenings are lively, but still warm in Florida!
From the community coming together to decorate for the Fall to pumpkin festivals, Anna Maria Island offers something for every kind of Halloween lover! Stay close to the fun with Anna Maria Island Accommodations, where our family-friendly rentals put you just steps from the beach and near all the festive happenings. Whether you’re here for trick-or-treating with the kids or adult-friendly costume fun, you’ll find the perfect place to relax and recharge after your spook-tacular day.
