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Monthly Guide

October Events on Anna Maria Island

Fall festivals and Halloween celebrations.

Best for fall visitors and families.

Oct 20, 2026

Matthew McCartney

Matthew McCartney is a Florida-based traveling musician whose soul-stirring performances echo through the Southeast like a beacon of raw, unfiltered passion....

OutdoorLive Music

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Oct 24, 2026

The Art Of...Sound and Story

We invite you to join us on Saturday, October 24, 5-7PM, for a special musical collaboration with the Sarasota Performing Arts Foundation called Sound and...

Live Music

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Oct 24, 2026

Something Is Beneath the Water: Legend of the Mangrove Murders: AMI Paddleboard and Kayak Adventures

Join AMI Paddle and The Center for a Halloween adventure on the water! Paddle through the mangroves of Neal Preserve after dark for an evening filled with fun,...

Outdoor

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Oct 25, 2026

Tony Tyler

Tony Tyler is a great musician with a very wide range. He thrives off requests so make sure to shout them out! He is accompanied by guitar, keyboard, and bass!...

Live Music

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Oct 27, 2026

Cody Moore

As a key member of The Hip Abduction, Cody Moore has toured extensively across the US, Canada, and the UK. His solo live-looping show takes that stage-tested...

Live Music

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Oct 29, 2026

Seven Nations

The story of SEVEN NATIONS is that of a truly original and determined band that began in New York City, with members now hailing from California, to Toronto,...

OutdoorLive Music

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Oct 30, 2026

Anna Maria Island Chamber of Commerce Trail of Treats

Please join us for our “Trail of Treats” on Friday October 30th at 4:00 PM at at the Anna Maria Island Chamber of Commerce! Address: 5313 Gulf Drive, Holmes...

Outdoor

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Oct 30, 2026

Island Trunk or Treat

Join The Center of Anna Maria Island and School for Constructive Play for a safe, fun, and FREE evening of early trick-or-treating! Friday, October 30th...

FreeFood & Drink

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Oct 30, 2026

Sunburnt Bois duo

Playing the songs you know, the songs you forgot, and a few future favorites in between, Miguel Lantigua and the Sunburnt Bois bring an energetic blend of...

Live Music

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Oct 31, 2026

AMI South End Presents Sundown Get Down – Halloween Spooktacular

Join us for a Halloween Spooktacular filled with family-friendly fun, costumes, candy, entertainment, and exciting activities for all ages! Bring your little...

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Every year in October

Annual events whose date this year is expected from past years but not yet announced by the organizer.

More event months

Browse a few other months without returning to the hub.

Plan your october events stay

Sandbox Beach House keeps you close to all the action while providing a quiet home base. Heated pool, walk to beach, and small dogs (35 lbs or less) welcome.