Fall Fun Activities in Seaside

Every season in SEASIDE® brings its own kind of magic. As Fall arrives, the pace begins to slow, inviting us to linger a little longer, spend more time together, and enjoy the simple traditions that make this time of year so special. From afternoons by the Gulf to evenings gathered around town, Fall in SEASIDE® is all about savoring the season at a slower pace.

Kicking off September with a celebration of Summer’s final days, our Labor Day Concert takes place on September 7th. Gather with family and friends at the Seaside Amphitheater from 6:30–8:00 PM for an evening of live music under the stars. Bring a blanket or lawn chair and join us as we come together to celebrate Labor Day and say farewell to another unforgettable summer in SEASIDE®.

ken and andi & friends Labor Day weekend seaside florida 30a

The end of summer doesn’t mean the fun slows down in SEASIDE®. October brings a new rhythm to town, with familiar traditions, seasonal events, and plenty of reasons to spend time together.

The Seaside Farmers Market continues every Saturday from 9 AM to 1 PM, bringing locals and visitors together for one of our favorite weekend traditions. Take your time wandering through the market, discovering fresh finds, local favorites, and something new around every corner. As the days get a little quieter and the holiday season comes into view, there’s something special about experiencing this beloved tradition in the Fall.

Central Square Cinema continues on Fridays at 7:00 PM, bringing one of our favorite Friday traditions into the Fall. As the sun sets, gather your family on the lawn, grab dinner or a sweet treat from one of our local merchants, and settle in for a movie beneath the stars. Bring a blanket or lawn chair and make an evening of it.

People sitting on grass at night watching animated movie outdoors on large inflatable screen in park setting.

And while some of our favorite traditions continue week after week, Fall in SEASIDE® also brings special events that happen just once a year. From festive celebrations to beloved community traditions, there’s always something to look forward to.

Every year, SEASIDE® comes alive with four-legged fun at the Annual Halloweener Derby & Dog Costume Contest! This year, join us on October 24 from 10 AM–2 PM for one of our favorite fall traditions. The celebration begins with the Dog Costume Contest, where pups of all shapes and sizes show off their best Halloween looks, followed by the main event, the Halloweener Derby! Watch as our speedy dachshunds race to the finish line while the crowd cheers them on. Bring the whole family, grab a bite from a local merchant, and spend the day celebrating one of our most beloved traditions.

halloweener derby seaside florida 30a

Halloween in SEASIDE® is a tradition filled with imagination, creativity, and a little bit of magic. Each year, October 31 transforms the town into a festive wonderland, with a new theme bringing the celebration to life, and this year’s theme is still under wraps! From creatively decorated stores and interactive stops to trick-or-treating throughout town, Halloween in SEASIDE® is a night the whole family looks forward to year after year. Wander through town, discover what’s around every corner, and join us for an unforgettable evening of Halloween fun. We can’t wait to reveal what we have planned for this year’s celebration!

halloween seaside florida 30a

As the holiday season gets closer, November brings one of SEASIDE®’s most anticipated traditions: the Seeing Red Wine Festival.

Held throughout Central Square and other venues around town, this four-day celebration of wine, food, and good company takes place November 5–8. From the Grand Tasting and Reserve Tastings to intimate dinners and spirited wine competitions, there’s something to look forward to at every turn. It’s a weekend made for gathering with friends, discovering something new, and raising a glass to the season. Learn more about the festival at the Seeing Red Wine Festival.

Two people wearing sunglasses at an outdoor wine tasting table with assorted bottles and a server pouring wine.

And while Fall may bring a different rhythm to our little beach town, there’s always something happening in SEASIDE®. From beloved traditions to new experiences, November is a wonderful time to slow down, spend time together, and enjoy the town in a different season. Come experience fall in SEASIDE® and make a few memories of your own along the way.

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