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  • Writer's pictureNancy 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.

Musical numbers will include Broadway Hits, Classical and Patriotic favorites. There are several seating options available for purchase suiting every budget. A portion of the proceeds benefit the Anna Maria Island Chorus and Orchestra.

  • $125 – VIP Ticket Includes: Table Seating for 1 person with delicious small plates by area restaurateurs, complimentary fine wine and select beer, luxury restrooms (tables seat 10)

  • $75 Ticket/Person - Seating on Concession Deck at Table for 4, includes 2 drink vouchers per ticket & option to purchase concessionaire food to be enjoyed at your deck seating

  • $50 – Ticket Includes: Concert Chair for 1 person with 2 drink vouchers per ticket & concessionaire food purchase options

  • $20 – Ticket Includes: General Admission for 1 person, bring your own seating with cash bar & concessionaire food purchase options

Participating restaurants are:

Beachhouse Restaurant, Coquina Beach Cafe, Harry's Continental Restaurant, The Lazy Lobster and Hometown Desserts.

Tickets can be purchased at EventBrite here.

Insider Tip!

For this event you can come as you are with flip flops on or dress in fancy cocktail attire.

Remember the entire event is on the sand so stilettos may not be advisable.

There's plenty of parking but if you'd like to drink take the Free Trolley!



November 9 - 10, 2019

Fisherman's Village of Cortez

and Swordfish Restaurant across the street

(off the island)

Saturday 9:00 am - 6:00 pm

Sunday 10:00 am - 6:00 pm

Cortez Fishing Boat

Head out to the 8th Annual Cortez Stone Crab and Music Festival in the historic fishing village of Cortez and the Swordfish Grill and Tiki Bar Restaurant across the street.

This is a FREE festival featuring stone crabs, colossal crabs and jumbo crabs. This event benefits Fishing for Freedom’s Manatee chapter and the children of Port St. Joe, the sister city of Cortez. Also some of the Festival proceeds will help cover lost wages for Cortez commercial fishermen affected by red tide.This year’s festival also is a hurricane relief toy drive for families hit hard by Hurricane Michael recently.

Did you know that there are 1,200 pounds of stone crab waiting to be consumed by festival goers? You can enjoy the sights, sounds and tastes of the Stone Crab Festival with live music on the big stage. Musicians include Berry Duane Oakley, son of original Allman Brothers Band bassist Berry Oakley. You can also listen to local favorites like Dr Dave Band and Doug Deming and the Jewel Tones.

Kids will love the Kid Zone and shop till you drop at the local artist booths and displays. We have a lot of talented artists around Anna Maria Island.

If you are traveling by boat look for Marker 49 and dock at the Swordfish Grill & Tiki Bar. If you are driving there is parking available at the FISH Preserve on 116th Street West, Cortez with shuttles to the festival. The best option hassle free is the Free island Trolley services.



Monday, November 11, 2019

Pine Avenue to City Pier Park

Anna Maria

(north end of the island)

1:00 pm - 2:00 pm

Be sure to get out and enjoy this parade and don't forget to stop and thank a veteran for their service and sacrifice to the country. The parade will start at City Hall about mid-way down Pine Avenue and walk north towards the City Pier Park.

The Veteran's Day Parade features, floats, the Privateer Pirates, marching bands and more, be sure to look up to the military fly-over!

The Anna Maria Island Historical Society will top off this event with a good old-fashioned Ice Cream Social at the Museum. It's Free!



Friday, December 6 - Sunday, December 8, 2019

Bradenton Riverwalk Pavilion

452 3rd Ave W. Bradenton, FL

(east of the island)

Check dates for time schedule

Located on the mainland in the town of Bradenton. The Bradenton Blues Festival runs all weekend. If you love the Blues then this is the music festival for you.

Not only do they offer an epic line-up of talented music artists but the local craft beer, delicious food is also worth the trip. Just 8 miles east of Anna Maria Island

Some time slots are free and there are also tickets for main events starting at $45.00. Drinks and snacks are available for an extra cost.



Friday, December 13, 2019 ~ 4:00 - 10:00 pm

Saturday December 14, 2019 ~ 11:00 am to 10:00 pm

Sunday, December 15, 2019 ~ 10:00 am to 10:00 pm

Coquina Beach

(south end of the island)

Located on the southern end of the island at Coquina Beach, enjoy music, dancing, and eating great seafood at this new event. Music line up includes:

A Fleetwood Mac Tribute Band

Billy Rice Band

Kettle of Fish

The Black Monkeys

The Verge

JP Soars

R. J. Howson

Dr Dave Band

Free admission! Enjoy the sounds of music, dance on the sand and shop the festival marketplace. For detailed information check out their website here.

Anna Maria Island Food and Wine Festivals - Anna Maria Island Home Rental



Saturday, October 26, 2019

Florida Maritime Museum

4415 119th St W, Cortez

(off island)

8:00 am - 1:00 pm

Discover and purchase unique marine antiques, nautical gear, dive gear, fishing gear and more! What's a Cortez event without live music and food? Visit this incredible area that is one of the oldest working fishing villages in the United States. Truly a great local experience.



Every Tuesday from October 2019 to May 2020

Pine Avenue to City Pier Park

Anna Maria

(north end of the island)

8:30 am - 2:00 pm

Every Tuesday from October to May you can head to the local Anna Maria Flea Market and pick up some local fresh produce to cook up in one of our vacation rentals. Don't forget that we completely outfit our kitchens with everything a chef would need including two grilling options (gas and charcoal).

In addition to the produce you can explore and grab great finds with arts and crafts and local creations Don't forget to hit up some of my fave shops along Pine Avenue like Island Cabana for women and AMI Outfitters for men.



Every Sunday from November 2019 to July 2020

Coquina Beach, Gulfside Park

2650 Gulf Dr. S., Bradenton Beach

(south end of the island)

10:00 am - 4:00 pm

Every Sunday from November to July you can soak up the sun while you shop the Coquina Beach Market. Here you can find books, clothes, jewelry, eats and treats. Often there is a band playing while you stroll and meander along the local vendors booths.

Coquina Beach has great amenities for everyone, including a play area for the kids, tons of parking and a 3 mile long pathway for hiking and biking. You can read all the amenities of Coquina Beach here on our INSIDER GUIDE TO THE BEST BEACHES of Anna Maria Island.



At Anna Maria Island Home Rental, we have luxurious waterfront accommodations. Enjoy a last minute getaway with one of our Fall Vacation Deals. We have gap stays and full weeks available. Contact us for information and a detailed quote!

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