Halloween in Seaside, Florida
Halloween By the Sea
Fall Events in Seaside, Florida
Summer may get the attention, but fall is when Seaside settles into a rhythm all its own.
The days are still made for the Gulf, while cooler evenings bring everyone back to Central Square. Costumes come out, dachshunds take their marks, wine glasses are raised, and some of SEASIDE®’s most beloved traditions return to town.
From Halloween celebrations for the whole family to a four-day wine festival, discover the events worth planning a fall getaway around.
Halloweener Derby & Dog Costume Contest
Ready, set, run.
One of Seaside’s most spirited fall traditions returns as dachshunds take over Central Square for the annual Halloweener Derby. The day begins with a dog costume contest, followed by the main event: a lively race to the finish line.
Equal parts competition and pure fun, the Derby brings together racing pups, creative costumes, families and plenty of cheering from the sidelines.
Halloween in Seaside
This Halloween, consider this your Golden Ticket.
Seaside transforms into a candy-colored world of pure imagination, where sweet surprises, whimsical treats and familiar characters await around every corner.
Families can dress for the occasion and make their way through town during Seaside’s annual trick-or-treat celebration, visiting participating merchants and discovering imaginative installations along the way.
Costumes encouraged. Curiosity required. And somewhere among it all, a Golden Ticket may be waiting.
Seeing Red Wine Festival
Fall calls for something worth raising a glass to.
The Seeing Red Wine Festival returns to Seaside for four days dedicated to exceptional wine, food and good company. The annual festival brings together vintners, winemakers, chefs and wine lovers for tastings and culinary experiences throughout town.
The weekend culminates in the Grand Tasting in Central Square, where wines from around the world meet cuisine from local chefs, live music and an afternoon spent together under the Florida sun.
Come for a tasting. Stay for the weekend.
Make a Weekend of Fall in Seaside
There’s more to fall here than what’s on the calendar.
Start Saturday morning at the Seaside Farmers Market. Take the long way through town. Spend an afternoon by the Gulf before heading back to Central Square for the evening. Explore the shops, find a table for dinner, or simply enjoy having nowhere else to be.
With some of the year’s favorite events filling Seaside for the first time.
Fall in Seaside: Frequently Asked Questions
When is Halloween in Seaside, Florida in 2026?
Halloween in Seaside takes place on Saturday, October 31, 2026, from 4–7 PM in Central Square. Families can trick-or-treat at participating merchants throughout town and discover imaginative installations along the way. Costumes are encouraged.
What is the Halloweener Derby?
The Halloweener Derby is Seaside’s annual dachshund race and dog costume contest, held in Central Square. In 2026, it takes place on Saturday, October 24. The day begins with the costume contest, followed by the race to the finish line.
When is the Seeing Red Wine Festival in 2026?
The Seeing Red Wine Festival returns November 5–8, 2026. The four-day festival features tastings and culinary experiences throughout Seaside and culminates in the Grand Tasting in Central Square, with wines from around the world, cuisine from local chefs and live music.
What else is there to do in Seaside in the fall?
Beyond the events calendar, fall is a great time to enjoy the Gulf with cooler evenings. Start Saturday morning at the Seaside Farmers Market, spend the afternoon on the beach, then head to Central Square to explore the shops and find a table for dinner. See all upcoming events in Seaside.
