Anna Maria Island was ranked the No. 3 beach in the U.S. for 2026 by U.S. News & World ReportNo. 3 beach in the U.S. for 2026 · U.S. News
Turquoise Gulf water under a sky of white clouds
AmIsland Monthly · October 2026

October on Anna Maria Island

Fall sunshine, local events, Gulf sunsets, and another good reason to come back to the island.

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Filmed by the AmIsland Properties family near Longboat Pass
Island Notes / October 2026

October on Anna Maria Island has a little of everything: the 25th BayFest on Pine Avenue, a beach 5K for the island's elementary school, Halloween fun for the kids, and long beach days that end with the sun going down over the Gulf.

It is also the last month of sea turtle nesting season, which officially ends Oct. 31.1 Here is our pick of what's happening, our first Restaurant of the Month, and a tip for getting around without your car.

01Festival

BayFest turns 25 on Pine Avenue

When
Saturday, Oct. 17, 10 a.m. to 9 p.m.
Where
Pine Avenue, City of Anna Maria
Hosted by
Anna Maria Island Chamber of Commerce

The Chamber's 25th annual BayFest takes over Pine Avenue for the day with live music, a classic car show, local vendors, food trucks, beer and wine.2

Staying at SeaCrest? Pine Avenue's boutiques and dining are an easy bike ride from the house.

Stay close: SeaCrest
02On the beach

Run the Dolphin Dash at Coquina Beach

When
Saturday, Oct. 10. Fun run 9:15 a.m., 5K 9:30 a.m.
Where
Coquina Beach pavilion by the playground, 2650 Gulf Drive, Bradenton Beach
Cost
$35 for the timed 5K, $15 for the roughly 1K fun run

Anna Maria Elementary's Dolphin Dash starts and finishes at the Coquina Beach playground. The timed 5K is for grown-ups and fast kids, and Fin's Fun Run heads from the playground to the Coquina Beach cafe and back.3

Coquina Beach is in Bradenton Beach, the same town as Island Breeze, and it is where the free island trolley's route begins.4

Stay close: Island Breeze
03Halloween

Halloween, island style

Three ways for the kids to trick-or-treat, plus a spooky paddle for grown-ups.

  • Oct24Sat

    Legend of the Mangrove Murders night paddle

    AMI Paddle and The Center lead a Halloween paddle through the mangroves of Neal Preserve after dark. Families about 6 to 7:30 p.m., adults 18+ about 8:30 to 10 p.m. Meets at The Center, 407 Magnolia Avenue, Anna Maria. $120.7

  • Oct30Fri

    Trail of Treats

    Costume contest at 4:30 p.m. at the Chamber, 5313 Gulf Drive, Holmes Beach, then trick-or-treating at participating island businesses from 5 to 6:30 p.m.8

  • Oct30Fri

    Island Trunk or Treat

    Decorated trunks and tables full of treats at The Center of Anna Maria Island, 6 to 8 p.m. Free.9

  • Oct31Sat

    Sundown Get Down: Halloween Spooktacular

    Historic Bridge Street in Bradenton Beach becomes a family Halloween party with costumes, candy, entertainment, local vendors and games, 2 to 8 p.m. Free.10

04Island life

Beach days, Gulf sunsets and Bridge Street

Not every day needs a plan. Spend the morning on the sand, cool off in the Gulf, and stay out for the sunset.

In Bradenton Beach, historic Bridge Street has boutiques, shops and restaurants and the Historic Bridge Street Pier.5 It is a short walk from Island Breeze.

A wide, shallow sandbar under blue sky and white clouds
A sandbar walk, filmed by the AmIsland Properties family
AMISLAND PROPERTIES · RESTAURANT OF THE MONTH · AMISLAND PICK Smoqehouse OCTOBER 2026
Restaurant of the Month · October 2026

Smoqehouse

Chef-inspired craft sandwiches and BBQ fusion · Bradenton Beach

The fries and their signature sauce are worth the drive. That's what we order every time, and it's a must-order.

The AmIsland Properties family

Smoqehouse calls itself "chef inspired. craft sandwiches. bbq fusion. fast casual."11 Don't expect a traditional barbecue joint: the kitchen cooks from scratch with fire and smoke and borrows ideas from cuisines around the world, turning them into handcrafted sandwiches, salads, soups and fries.12

It's fast casual, so it fits right in between beach sessions: order at the counter, eat, and get back to the sand.

What we order
  • The fries with their signature sauce

The sea turtles keep coming back. So will you.

Plan your stay

Make AmIsland Your Home Base

Two homes, two different ways to do the island. Pick the one that fits your trip, then check the dates.

Island Breeze, Bradenton Beach
Bradenton Beach

Island Breeze

  • 2 bedrooms · 2 bathrooms · sleeps up to 6
  • Private saltwater pool and private hot tub
  • Walkable to the beach, restaurants, shops and historic Bridge Street

Best for: Guests who like walking to dinner and having more going on nearby

View Island Breeze
SeaCrest, Holmes Beach
Holmes Beach

SeaCrest

  • 2 bedrooms · 2 bathrooms · sleeps up to 6
  • Private saltwater pool
  • About 200 steps from the beach, on a quieter residential street

Best for: Quiet mornings, long beach days and easy beach access

View SeaCrest
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Sources
  1. The Anna Maria Islander, "Nesting notes: Winding down in October" (Oct. 7, 2025). islander.org
  2. Anna Maria Island Chamber of Commerce, 25th Annual BayFest; The Suncoast Post (Oct. 2, 2026). annamariaislandchamber.org · suncoastpost.com
  3. AME Dolphin Dash 2026, RunSignup. runsignup.com
  4. Anna Maria Island Chamber of Commerce, Island Trolley. annamariaislandchamber.org
  5. Bradenton Area Convention and Visitors Bureau, "Explore the Gulf Island Ferry Stops". bradentongulfislands.com
  6. Manatee County Area Transit (hours); Anna Maria Island Chamber of Commerce (free, route). mymanatee.org · annamariaislandchamber.org
  7. Anna Maria Island Chamber of Commerce, Legend of the Mangrove Murders. annamariaislandchamber.org
  8. Anna Maria Island Chamber of Commerce, Trail of Treats. annamariaislandchamber.org
  9. Anna Maria Island Chamber of Commerce, Island Trunk or Treat. annamariaislandchamber.org
  10. Anna Maria Island Chamber of Commerce, Sundown Get Down Halloween Spooktacular. annamariaislandchamber.org
  11. Smoqehouse. smoqehouse.com
  12. Bradenton Area Convention and Visitors Bureau, Smoqehouse AMI listing (description and address); Discover Bradenton (address). bradentongulfislands.com · discoverbradenton.com

Dates, times and prices come from each organizer's listing as of October 4, 2026. Plans can change, so check the source before you go.