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Halloween on Anna Maria Island: My Insider Guide

Updated: October 2026

Halloween on Anna Maria Island still feels like a small town celebration. Between family trick-or-treating routes, a Chamber-run signature event, and a handful of spookier day trips off the island, there is enough here to fill the whole week leading up to the thirty-first. If you are still working out the rest of your trip, my Things to Know Before Visiting Anna Maria Island: My Insider Guide covers the basics before diving into the season’s events.

On the Island

Bridge Street Ghost Walk

For a Halloween evening without kids in tow, Sarasota Suncoast Tours runs a themed walking tour on Bridge Street each October, built around the stories behind the Bride of Bali Hai, longtime local George Emerson Bean, and the island’s Al Capone lore, along with the history behind the bridges connecting the three island cities. The tour runs most October evenings and books up, so reserve ahead through the operator’s website.

Crochet Ghost Workshop

Center of Anna Maria Island
941-778-1908
October 6 & 20
5:30 PM to 7:30 PM
Cost · $40 for members, $45 for non-members

Learn the basics of crochet while creating your own spooky little ghost friend. This hands-on workshop is perfect for beginners, with all materials provided and no prior experience needed. Pre-registration is required. Call The Center to reserve your spot.

DJ Dance Halloween Party

  • 5337 Gulf Drive · Holmes Beach
  • 941-251-3930
  • October 31
  • Live Music · Tuesday, Thursday, Friday – Sunday · 7:00 PM to 11:00 PM
  • Live Music · Saturday · 3:00 PM to 6:00 PM
  • Happy Hour · 3:00 PM to 6:00 PM

Freckled Fin Irish Pub in Holmes Beach traditionally hosts a costumed DJ dance party for the over-21 crowd in late October, a good way to extend the Halloween spirit into the evening for visitors without kids.

Fall Fest at The Center

Fall Fest at The Center of Anna Maria Island is a long-running island tradition with a great pumpkin theme. Presale ticket information and full event details are typically announced closer to the date, so watch The Center’s page if you want tickets in advance.

The Final Feast at The Feast AMI

  • 5406 Marina Drive · Holmes Beach
  • 941-778-5092
  • October 30
  • Happy Hour · Daily 4:00PM to 5:30 PM
  • Price · $90 per person

For something more indulgent than trick-or-treating, The Feast AMI hosts The Final Feast, a one-night six-course dinner with a cocktail pairing for each course. Reservation only, with one seating at one table, so book ahead if you want in.

Florida Beach Horses Witch Ride

For something completely different, Florida Beach Horses hosts a Witch Ride, a horseback cruise where riders in witch and wizard costumes parade along the shoreline in the evening. Tickets are limited and there is no online booking, so call ahead to reserve a spot.

Island Trunk-or-Treat at The Center

The Center of Anna Maria Island and School for Constructive Play host a safe, early trick-or-treat evening for families. Palm Ave behind The Center closes from 6:00 PM to 8:00 PM, creating a safe space for families to walk, explore decorated trunks and tables, and collect treats. Come dressed up and ready for a fun night with the island community.

Individuals and businesses are invited to host a car or table and hand out treats. There is no cost to participate, but advance registration is required, and for the safety of all participants, treats must be store-bought and commercially factory-wrapped. Set-up begins at 5:00 PM.

Macrame Pumpkin Decor Workshop

Get creative and make your own macrame pumpkin. No experience is needed and all materials are provided. Pre-registration is required. Call The Center to reserve your spot.

Pine Avenue Trick-or-Treating

Pine Avenue in the City of Anna Maria is one of the coziest spots on the island to trick-or-treat. Local boutiques and shops decorate their storefronts and hand out candy to costumed visitors, and the walkable, small-town feel makes it an easy evening for families with younger kids.

Something Is Beneath the Water: Legend of the Mangrove Murders

  • Neal Preserve
  • October 24
  • Paddleboard · $60, 9 available, 250 lb weight limit
    Single Kayak · $60, 10 available, 250 lb weight limit
    Double Kayak · $100, 10 available, 500 lb weight limit
    Double Full Clear Kayak · $120, 10 available, 550 lb weight limit

AMI Paddleboard and Kayak Adventures hosts a Halloween paddle through the mangroves of Neal Preserve after dark, with a little fun, fright, and mystery mixed in. Parking is on the right side of the Manatee Bridge next to The Compass Hotel. Paddleboards may accommodate one child with an adult within the 250 lb combined weight limit. Space is limited and advance registration is required.

First Trip · Kids and Families
6:00 PM to 7:30 PM (approximate), check-in at 5:40 PM
Ages · 17 and under, or adults accompanying children who cannot paddle independently

Second Trip · Adults
8:30 PM to 10:00 PM (approximate), check-in at 8:10 PM
Ages · 18 and up

Trail of Treats

  • 5313 Gulf Drive · Holmes Beach
  • October 31
  • 4:00 PM to 6:30 PM
  • Admission · free

The Trail of Treats is the island’s signature Halloween event, hosted annually by the Anna Maria Island Chamber of Commerce. Families gather for a kids’ costume contest, divided into four age groups with trophies awarded to the winners, and the contest kicks off the event before trick-or-treating continues at participating businesses across Anna Maria, Holmes Beach, and Bradenton Beach. It pairs well with a stop for dinner along the same strip. My guide to Bridge Street on Anna Maria Island covers the shops and restaurants along the way.

Off the Island

BooFest on Main Street

BooFest on Main Street fills with trick-or-treat booths, inflatables, balloon twisters, and live entertainment. It is a bit of a drive from the island but a popular option for families looking for a well-organized night out.

Goblin Gathering

  • GT Bray Park · 51st Street West · Bradenton
  • October 16
  • 4:00 PM to 7:00 PM
  • Admission · free

Goblin Gathering is a family-friendly Halloween event at GT Bray Park featuring inflatable attractions, hayrides, costume contests, a petting zoo, and a photo booth. Costume contest sign‑ups begin at 4:00 PM and judging starts at 6:00 PM.

Haunted Run

  •  Heritage Harbor Park · River Heritage Boulevard · Bradenton
  • October 17

Anyone who wants to stay active through the season can look for the Haunted Run, a costumed race held in the area during daytime hours. Whether you are racing for time or just there for the costumes, the Haunted Run is a fun, offbeat way to spend a fall morning.

Howl-O-Scream at Busch Gardens

  • 10165 McKinley Drive · Tampa
  • Through October 31
  • Admission · $34 to $500

Anyone chasing a bigger scare can make the drive to Tampa for Busch Gardens’ Howl-O-Scream, which transforms the park into haunted houses, scare zones, and live shows. It is not on the island, but it is a reasonable day trip for visitors wanting a more intense Halloween.

Hunsader Farms Pumpkin Festival

  • 5500 County Road 675 · Bradenton
  • October 10–11
  • October 17–18
  • October 24–25
  • 9:00 AM to 5:00 PM
  • Admission · $15 ages 10+ · $5 ages 5–9 · Free under 5
  • Parking · $5
  • Cash only (some vendors accept cards)

A short drive from Anna Maria Island, Hunsader Farms hosts its annual Pumpkin Festival across select weekends in October, with hayrides, a corn maze, scarecrow displays, craft vendors, live music, and pony rides. On October 25 they host a costume contest and dogs are welcome.

Want more real-time tips and honest answers about Anna Maria Island? Join Anna Maria Island Insider, my Facebook group built on one simple rule: real, helpful answers only. Join the group.

Coastal Close

Halloween on Anna Maria Island blends coastal relaxation with just enough spooky fun to make it memorable. Whether you spend the evening trick-or-treating down Pine Avenue or venture off-island for bigger thrills, it is an easy season to build a trip around.

— izzy