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Anna Maria Island Trail of Treats

Anna Maria Island is one of Florida’s best-kept secrets. This welcoming community is not home to high-rises and tons of tourists, but instead, you will find quaint homes and shops run by locals and loved by all. Although Anna Maria Island is lovely any time of the year, it’s especially nice in the fall time. It is still warm enough to enjoy the beach, but the evening breezes help cut some of the heat and still allow you to enjoy the outdoors. AMI particularly comes alive during Halloween, and the Trail of Treats is one of their most popular events. Read on to learn all about this fun event just moments away from our city of Anna Maria vacation rentals.

Kids holding Halloween sign in their costumes


The Trail of Treats has been an Anna Maria tradition for years, drawing locals and visitors from miles around. This family-friendly event is perfect for everyone from the youngest trick-or-treaters to the parents and grandparents as well. All visitors are welcome to wear their costumes and collect as much candy as they can.

Local businesses register to participate in the Trail of Treats through the Anna Maria Chamber of Commerce. Businesses contact the Chamber a couple of months before Halloween, and then the Chamber of Commerce releases a flyer with the participating businesses. There are participating businesses in all three cities on Anna Maria Island, and each business is in a safe and secure location so you don’t have to worry about your young kids running all over town to collect treats.

More Information

The Trail of Treats will occur on Halloween and will begin at the Anna Maria Chamber of Commerce. Be sure to arrive early if you wish to register for the costume contest! For the contest, there are four different age groups so that everyone gets a fair shot at the prizes. Typically, this event takes place on Halloween evening around 4 p.m. until 8 pm. Additional information about the Trail of Treats will become available closer to Halloween.

This event is also a great opportunity for you to speak to local businesses and with artisans in the area. Not only will you be contributing to the local economy, but you can also find a one-of-a-kind souvenir to remember your trip.

Close up of Pumpkin Carving in Bradenton, FL

Other Halloween Events near Anna Maria Island

The Trail of Treats isn’t the only way you can get involved in AMI on Halloween. One of the longest-running Halloween events on the island is the Hunsader Farms Pumpkin Festival, celebrating its 28th year in 2019. This festival occurs all throughout October, and you will be able to find entertainment like live music and shows, hayrides, a corn maze, and delicious homemade food. Many activities are free with your admission price, while some will charge a small additional fee.

If you are a master pumpkin carver, you won’t want to miss the Sertoma Pumpkin Patch in Bradenton. Each Saturday in October, you can select your favorite pumpkin to carve with whatever design you please. Your purchase will benefit local charities and scholarships, so you can feel good about where your money is going. Another great event is just down the road in Sarasota at Selby Gardens with the Selby Gardens Spooktacular. Put your kids in their costumes and let them trick or treat while exploring the gardens and learning more about the nature of the area. This is an annual event that is fun for all ages.

There are tons of fun things to take part in throughout the Halloween season on Anna Maria Island, and this event is just one of many. Of course, there are plenty of activities to enjoy on AMI all year round, like hanging out on the beach, indulging in fresh seafood, or find a unique souvenir to take home. At the end of a long day of trick-or-treating, you can return to our AMI vacation rentals to unwind and start eating your candy! For more information on Halloween events in the area as well as our full range of rental properties, contact us today!