anna maria island





  • Nancy McAleer

Discover ~ Fall Festivals on Anna Maria Island, Florida

Updated: Dec 13, 2019

Insider Guide to Fall Festivals on Anna Maria Island - Anna Maria Island Home Rental

The Fall season is one of the best times to visit Anna Maria Island. There is so many benefits to carving out some much needed vacation time here, the accommodation rates are at their lowest, the tourist traffic is down, the temperatures are still hot (86° average in October) and the festivals!!!! There are a ton of them, so let me list our favorites in this Ultimate Fall Festival List.

If you are interested in the Fall Flea Markets scroll straight down to the bottom for a full list.



Saturday, October 19, 2019

Pine Avenue, Anna Maria

(north end of the island)

10:00 am - 9:00 pm

Bayfest on Anna Maria Island is a great family and friends musical event. Drop by and enjoy a fun filled day in the City of Anna Maria on Pine Avenue where they close off the street. Anna Maria is located on the north end of the island within walking distance from our vacation rentals.

This will be Bayfest's 19th year running. It not only offers music all day long, there is a classic car show, kids zone and delicious food and drinks. There will be bands playing on the main stage as well as local bands dotted along Pine Avenue for your enjoyment as you stroll along exploring the local shops. Arts and crafts booths will also be featured on Pine Avenue. If you appreciate beautiful classic cars which include antique, custom muscle cars, street rods, you will love the more than 100 Classic Cars showcased during Bayfest. There should be over 100 cars to enjoy this year! The kids will be enjoy the fun kids zone and especially the bouncy houses and the Privateer's Amazing Pirate Ship.

Parking Options:

  • Take the free AMI Trolley to Pine Avenue

  • Park at Crosspointe Fellowship Church at 8605 Gulf Dr. North Holmes Beach, there is plenty of room here. Then hop on the free dedicated trolley shuttle to Pine Ave

  • Park only where a designated spot exists or risk being ticketed or towed.


Mike Sales – Emcee – 10 AM – 9 PM Trevor Bystrom 10:30 AM – 11:30 PM

Memphis Rub 12 PM – 1:30 PM SoulRCoaster 2 PM – 4 PM Dr Dave Band 4:30 PM – 6:30 PM​

Karen & Jimmy Band 7 PM – 9 PM

Music Festival - Anna Maria Island Home Rental


What's Bayfest without food? We love love love the local delicacies on Anna Maria island so this is a great opportunity to sample from some of the best restaurants on the island.

Eliza Ann's Coastal Kitchen - we love their southern fried chicken! Crispy, juicy and amazing!

The Ugly Grouper - has really great chicken wings and pub grub

The Feast specializes in mouth poppers like coconut shrimp and conch fritters. Why do I love fried food so much? Cause it's amaze-balls!

Don't miss out on The Waterfront Restaurant who last year offered grouper tacos and pork carnitas. Their fish tacos made it into the Anna Maria Island Beach Life TOP 5 Fish Tacos Smackdown. We've got the recipe here!

There's a few other notable foodie vendors such as T & L BBQ, Churrolicious, Gran Arepa, Kona Ice, Tropi-Coco, Tyler's Gourmet Ice Cream, and more to come!


This event is free to the public but is wise to bring your wallet and enjoy the food and drink offerings along the street, as well as the craft booths set up and of course the fab and totally original local boutiques featured on Pine Avenue.

Insider Tip! There is limited parking available due to Pine Avenue being closed off so keep the car at home and take the free Island Trolley. Crosspointe Fellowship Church at 8605 Gulf Drive, Holmes Beach has a large parking lot. Park there and ride the free trolley that will be shuttling people directly from the church to the City Pier at the end of Pine Avenue. Need the schedule? Here it is.. FREE TROLLEY SCHEDULE

Better yet, get the transit app for real time information. Apple App - Google App - Choose transit authority as Manatee County or MCAT



November 2, 2019

Manatee Public Beach

4000 Gulf Dr., Holmes Beach

(middle of the island)

8:00 am - 12:00 pm

Sandblast Sand Sculptures - Fall Events Anna Maria Island Florida

Sandblast is a fun, family event drawing you out to the natural beauty of Anna Maria Island's beaches. If you aren't familiar with our gorgeous award winning beaches take a look at our INSIDER GUIDE TO THE BEST BEACHES of Anna Maria.

Amateur and professional sculpture builders take part as teams to create these incredible sculptures in the sand. Want to find out more about what it takes to be a professional sand sculpture? Read our interview with "Sandtastic" here.

Learn FREE insider tips, the professional tricks and their techniques from the Sandastic professional team from Thursday to Friday at sunset.

The competition itself will be held Saturday 9:30 am to 2:00 pm. Registering your own team is as easy as making a donation. You can do that here.

Insider Tip! This is a great event to teach the kids about respecting the beach in a fun and exciting way. You can view the sculptures entirely after the competition on Saturday, November 2, 2019 until the natural elements return them to a regular beach again.



The Second Friday of every month

(November to February)

Exception First Friday during the month of December

The ArtsHop event isn't actually a festival it's more like a great art tour around the different villages on the island. Celebrating the arts, culture and heritage of Anna Maria Island. It's a self guided tour through the different art galleries and shops where you can see live demonstrations of artwork like glass blowing, mosaics, photography, painting, henna tattooing and more! Some locations will have live music provided by The Ugly Grouper.

This is a FREE event for all ages to enjoy and is located in the heart of each village on separate dates so you can hit one or go to them all.

Don't miss out on the Island Players Theater Group performances. Something fun and different to do while on the island. Evening performances run Tuesdays through Saturdays at 8 pm and Sunday matinees's at 2 pm. Purchase tickets at Island Players website.

The proceeds will go towards assisting Island Turtle Watch and Shorebird Monitoring group in their conservation efforts and awareness for Anna Maria Island shorebirds. You can visit for more information.



Saturday, November 9, 2019

Coquina Beach, Gulfside Park

2650 Gulf Dr. S., Bradenton Beach

(south end of the island)

4:30 am - 7:30 pm

Symphony on the Sand is a musical and gourmet feast with the Gulf sunset as your backdrop. There is simply no more of a divine way to listen to the symphony than directly on the sand surrounded by nature. It's incredible!

The award winning Anna Maria Island Chorus and Orchestra will be playing for your enjoyment.

Sample the delicious small plates and cocktails from the local restaurants in the area while listening to the symphony.