5 Fun Fall & Holiday Events in Anna Maria

While you are busy browsing Anna Maria Island vacation rentals, consider booking your visit during the fall or winter. You might think this is the ‘off-season’ for AMI, but there are plenty of events on Anna Maria Island.

Just check out these fun Anna Maria fall and holiday events that will be happening this year.


Looking for things to do with kids? Then why not come during Halloween? There is plenty to do!

Every year, Hunsader Farms hosts a Pumpkin Festival. 2019 marks the 28th annual Pumpkin Festival and will feature 14 live shows, live music, a craft show, pony rides, hayrides, a petting zoo, a zip line, and – of course – pumpkins. A lot of these events are free with admission, which is $10 for those 11 and over; children 10 and under are free. Parking is $5.

The event is happening on October 12 – 13, 19 – 20, and 26 – 27. It goes all day from 9 a.m. to 5 p.m. You can find Hunsader Farms just off of Waterbury Road in Bradenton.


Bayfest Street Festival is one of the events in Anna Maria that should not be missed! Held in the middle of October, Bayfest takes place on Pine Avenue on Anna Maria Island.

Come out to Pine Avenue on Saturday, October 19 from 10 a.m. to 9 p.m. for all the free events. There is a classic car show that starts at 10, and live music goes all day. Dozens of food, refreshment, and arts and crafts vendors will line the street. It’s a family-friendly event, so bring the kids along for a great time!

renaissance fair by anna maria island
Photo from Shutterstock


Before you stuff yourself at one of the many places to eat on Anna Maria Island, head over to Sarasota for a journey back in time to medieval Europe.

The Sarasota Medieval Fair runs every weekend in November from 10 a.m. to 5:30 p.m. each day. It is a rain or shine event. Tickets can be purchased as a 2-day Flex Pass, 4-day Flex Pass, Season Pass, or as Single Day Tickets. You can add VIP access to your ticket or choose to do the Pub Crawl, which allows you to skip the long lines for the three pubs that will be serving food and spirits. Take note: Parking is free and always in abundance.

Expect to find all kinds of entertainment, from jousting to human combat chess! It’s fun for the whole family, and proceeds go to multiple non-profit 501 (c) (3) organizations.


Plan on coming to AMI during Christmas break? Then you should check out Holiday of Treasures on Pine Avenue. This annual event occurs in early December and is co-sponsored by the Anna Maria Island Sun and the Anna Maria Island Historical Society.

During this event, merchants along Pine Avenue remain open until 8 p.m., which is when the event ends. The AMI Historical Museum hands out free cider and cookies, and the Roser Memorial Community Church’s Joyful Noise Children’s Choir holds a free concert outdoors at the Historical Park.

Before the event starts, you can take the kids to meet Santa at the City Pier Park. It is the best way to initiate the Christmas holiday on AMI.

Plan Your Visit

The fall and holiday season is perfect for visiting AMI. Contact us today for information on all of our favorite Anna Maria Island vacation rentals!

New Year’s

Leave your Anna Maria Island pet-friendly rentals and ring in the New Year. Watch the ball drop from The Beach House Waterfront Restaurant on Gulf Drive. They serve dinner until 10 p.m. on New Year’s Eve, so get full on some grub and lift your spirits with a delicious drink or two.

Then, head out to the beach with a blanket to watch the fireworks or take them in from the restaurant’s porch. Either way, you are guaranteed a memorable entry into the New Year.