Outdoor holiday ballet performance with dancers in festive costumes in front of a large lit Christmas tree

HOLIDAYS

Seaside in Winter: A Quieter Season on the Gulf

Why winter in Seaside, Florida may be the town’s best-kept secret

Most people know Seaside in the summer. Fewer know it in the winter, and that is exactly what makes it special.

The crowds thin out. The beach stretches a little longer. Mornings call for a sweater and a second cup of coffee, and evenings bring sunsets that seem to linger over the Gulf. Seaside in the winter is still the same town, with its pastel cottages, white picket fences and sandy paths. It just moves at a slower, softer pace.

From the start of the holiday season to a celebrated songwriters festival and a February race weekend, here is what winter in SEASIDE^® has in store.

The Beach in Winter

Same Gulf. More room to breathe.

The water may be a little too brisk for a swim, but winter is when the beach becomes a place to simply be. Take a long walk along the shoreline. Watch the light change over the water. Bring a jacket, find a spot in the sand and stay for the sunset.

Back in town, the sidewalks and sandy paths are made for exploring on foot or by bike, with no rush to be anywhere at all.

Holidays in Seaside

Seaside Holiday Parade & Turn on the Town: Saturday, November 28, 2026 | 3–8 PM | Seaside Amphitheater

Winter starts with a celebration.

The holiday season in Seaside begins with Turn on the Town, the annual tradition featuring the Seaside Holiday Parade, when the community gathers at the Seaside Amphitheater as the town lights up for the holidays. More holiday events will be added to the Seaside events calendar as they are announced.

Preview the Holiday Season in Seaside

30A Songwriters Festival

January 15–18, 2027 | SEASIDE^® & venues along 30A

Where the song comes first.

Each January, some of music’s most celebrated songwriters come to 30A to share the stories behind their songs. In 2027, SEASIDE^® is home to one of the festival’s two main stages, and the festival kicks off on Friday night with headliners at the Seaside Amphitheater.

Come for the music, and stay for the long weekend in between sets.

SEASIDE SCHOOL^™ Half Marathon + 5K

Race Day: February 14, 2027 | Race Weekend: February 11–14 | Seaside

Lace up. Race weekend is coming.

Each February, runners make their way to Seaside for the SEASIDE SCHOOL^™ Half Marathon + 5K. Whether you are chasing a personal best in the half marathon, running the 5K or cheering from the sidelines, it is a weekend with plenty of energy in town.

In 2027, race day falls on Valentine’s Day, so plan to celebrate with a well-earned dinner for two.

Long Lunches and Slow Afternoons

Slow down and stay a while.

Winter is the season for lingering. Settle in for a long lunch, or watch the sun set over dinner at Bud & Alley’s, serving oceanfront dining in Seaside since 1986. Explore all of the options on our dining guide.

In between, take your time in the shops of Seaside, from coastal clothing and hats to jewelry and gifts. Hours can vary by merchant, so it is always a good idea to check ahead.

Why Winter Is the Season to Stay a While

More time. More space. More Seaside.

Winter is an easy time to settle in. Book a cottage or home in town, unpack for longer than a weekend and get to know Seaside the way the people who live here do: one walk, one sunset and one long lunch at a time.

Whether you are coming for the holidays, the music or the race, or simply for a quieter week by the water, Seaside will be ready for you.

Explore Winter Events in Seaside

Seaside in Winter: Frequently Asked Questions

Is Seaside, Florida worth visiting in the winter?

Yes. Winter in Seaside brings a quieter pace, fewer crowds and long walks on the beach, along with the start of the holiday season, the 30A Songwriters Festival in January and the SEASIDE SCHOOL™ Half Marathon + 5K in February.

What is the weather like in Seaside in the winter?

Winter in Seaside is generally mild, with comfortable days and cooler mornings and evenings. Pack layers, including a light jacket or sweater for beach walks and evenings outdoors.

What events take place in Seaside in the winter?

Winter in Seaside begins with the Seaside Holiday Parade and Turn on the Town on Saturday, November 28, 2026. The 30A Songwriters Festival takes place January 15–18, 2027, with a main stage at SEASIDE®, and the SEASIDE SCHOOL™ Half Marathon + 5K takes place on February 14, 2027.

Can you go to the beach in Seaside in the winter?

Yes. The beach is just steps from town year-round. While the Gulf is cooler in winter, it is a beautiful season for shoreline walks, quiet afternoons in the sand and sunsets over the water.

Do restaurants and shops in Seaside keep the same hours in winter?

Hours can vary by merchant, so we recommend checking with individual restaurants and shops before your visit, and booking ahead for holiday and event weekends.

Outdoor holiday ballet performance with dancers in festive costumes in front of a large lit Christmas tree

October 15, 2026

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Palm trees wrapped in lights surrounding a festive outdoor plaza with people gathering around a lit holiday tree at dusk

EVENTS Family Fun HOLIDAYS

Holiday Lineup

The season brings dazzling entertainment, festive ambiance, and a merry good time

By Wendy O. Dixon

Bright red parade truck carrying large inflatable dog and balloons, surrounded by spectators taking photos.

Three carolers in Victorian costumes sing outside a festively decorated building with wreaths and candy cane balloons.

Children and adults wearing festive hats ride in a red car during holiday parade on sunny day.

Beginning Thanksgiving Day weekend with the showing of the beloved “Nutcracker” ballet and ending with a New Year’s Eve spectacular celebration, Seaside celebrates the most wonderful time of the year by preserving traditions and making memories.

Many families make Seaside their home away from home, where they can enjoy a beachside Thanksgiving or Christmas that can include a beach-themed tree trimming and a Gulf Coast-inspired holiday feast.

Seaside merchants also get into the spirit, with gorgeous decorations that sparkle and twinkle.

Holiday Events

The holiday season begins Sunday, Nov. 23, with a performance of “The Nutcracker,” based on the critically acclaimed Russian ballet set to Tchaikovsky’s beloved score. From the ballet that launched a national holiday tradition, dancers will perform under the stars at the Seaside Amphitheater. “The Nutcracker” performance is the result of the vision of Seaside co-founder Daryl Davis, who introduced performance arts in Seaside. The show will be held at 5 p.m. and is free to the public.

Friday, Nov. 28, grab your blankets and head down to the amphitheater for a holiday edition of Central Square Cinema on the lawn in Central Square. The featured movie is “The Grinch (animated),” a classic for all to enjoy.

The festive events continue Saturday, Nov. 29, with Turn on the Town. Hosted by the Merchants of Seaside, the day includes a parade and the annual tree lighting ceremony. The event features live music and a special appearance by Santa Claus. Santa, master of ceremonies for the evening, will invite all of the kids to join him in front of the stage for a sing-along before magically brightening up the town. Then, the countdown begins in unison to light the 24-foot Christmas tree, as all of downtown Seaside is illuminated with bright, holiday lights. Following the lighting ceremony, bring your camera for photos with jolly ole Saint Nick.

Additional events in December include a concert under the stars, more photo ops with Santa, and the New Year’s Eve celebration. More details to follow in the winter issue of The Seaside Times.

September 24, 2025

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Handlers crouch beside their dachshunds behind orange fence for a dog race, crowd watches outdoors.

HOLIDAYS

Fall Festivities

This October, everyone can be your favorite character, even your dogs.

By Wendy O. Dixon

Two people in red aprons holding boxes with dachshunds dressed as hot dogs at an outdoor event.

Two people dressed as Scooby-Doo characters pose beside a dog in a themed wagon outdoors.

Smiling couple holding a small dog and a Seaside Style bag at an outdoor event.

Brown dachshund dog on grass being gently held by person near orange event fencing.

Like many small American towns, Seaside celebrates the fall season with nostalgia and a bygone spirit. October brings ideal weather, as well as some spooky good events.

Events

And they’re off. The crowd cheers. Down the stretch they come — a long stretch for these athletes.

This time each year, Seaside goes to the dogs, as man’s best friends and their beloved humans sprint to the Halloweener Derby. Celebrating its 15th anniversary, the Halloweener Derby returns for all dog lovers. The event, held Saturday, Oct. 25, starting at 10 a.m., includes a dachshund race and dog costume contest. Make plans to be in Seaside for the hilarious races as the short-statured pups run like the wind toward their cheering owners, or get distracted and circle the lawn looking to sniff a new friend.

But winning by a nose — still a long length for a wiener — is not the point for this race. While dachshund racing can be a serious sporting event, the Halloweener Derby race is quite informal. There are no age divisions, and entrants are not bred for racing. Dachshunds aged three months and older can race in the derby. Race officials don’t ask for a dog’s papers, but it is limited to dogs that are obviously dachshunds.

It will be a fun day of dog races, pageantry, fancy costumes, trophy presentations, photo ops, and entertainment — all in celebration of canine companions.

The derby helps support various charities and dog-friendly non-profits around town.

Then comes Halloween, Friday, Oct. 31, at 4 p.m. This year’s theme is “Wizard of Oz.” Follow the yellow-brick road, stopping to collect goodies from the Seaside merchants during the town’s Trick-or-Treat event. The Seaside Post Office will be reimagined in the town’s version of the Land of Oz. Get in on the fun by dressing as one of the famous characters, but all ghosts and goblins are welcome in any size or shape. And later, enjoy a showing of the movie “Wizard of Oz” in the Seaside Amphitheater.

September 24, 2025

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Couple stands inside market booth displaying colorful handmade bags and crafts at outdoor artisan fair.

EVENTS HOLIDAYS

Celebrate the Season at the 2025 SEASIDE® Holiday Market!

The most magical time of the year is just around the corner, and there’s no better place to celebrate than in Seaside, Florida! We’re thrilled to announce that vendor applications for the 2025 SEASIDE® Holiday Market are now open. Join us December 6-7 to showcase your artisan creations and holiday gifts in a setting brimming with festive charm.

Vendors will have the opportunity to display their products in a 10×10 tent with a 6’ table and linen included, creating a warm, inviting space for holiday shoppers. There is a $250 participation fee, and applications are due October 17, 2025. Successful applicants will be notified by October 31, 2025.

SEASIDE® Merchants are encouraged to participate at no cost, making this the perfect chance to share your holiday offerings with the community and visitors alike.

From twinkling lights to festive music, the SEASIDE® Holiday Market is more than a shopping experience, it’s a beloved seasonal tradition where families, friends, and neighbors gather to celebrate the joy of the season. Don’t miss your chance to be part of this magical event!

Apply today and make your holiday season sparkle in Seaside!

APPLY HERE

September 15, 2025

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HOLIDAYS

Celebrate the Magic of the Holidays in Seaside, Florida

Holidays in Seaside, from Turn on the Town to the last gift on the list

Snow may never fall on Scenic Highway 30A, but the holidays still find their way to Seaside.

The days stay mild enough for a walk on the beach. The evenings bring everyone back to Central Square. And when the town lights up for the season, it feels like the whole community has come together to celebrate.

Christmas in Seaside is less about checking things off a list and more about slowing down long enough to enjoy the season together. Here is what to know as you start planning the holidays in SEASIDE^®.

Seaside Holiday Parade & Turn on the Town

Saturday, November 28, 2026 | 3–8 PM | Seaside Amphitheater, Central Square

Where the season officially begins.

Every holiday season in Seaside starts with Turn on the Town. The annual tradition, featuring the Seaside Holiday Parade, gathers the community at the Seaside Amphitheater as the town lights up to welcome the holidays.

Bring the whole family. Arrive early. Stay for the lights.

Holiday Shopping in Seaside

Gifts with a story behind them.

Skip the mall this year. The shops of Seaside are just a short walk from one another, which makes holiday shopping feel more like an afternoon stroll than a chore.

Find coastal style at The SEASIDE Style^® and Kids + baby by The Seaside Style^®, a new favorite hat at Headley Hat Co, or a piece of permanent jewelry at Lala Links to remember the trip by.

Gather Around the Table

The best part of the holidays is who you share them with.

For a holiday dinner by the water, Bud & Alley’s has been serving oceanfront dining in Seaside since 1986. Find more places to gather on our dining guide, and book ahead for busy holiday weekends.

Make It a Holiday Stay

The best traditions are the ones you come back for.

Seaside was designed for walking, so Central Square, the shops and the beach are never far from your front porch. Settle into one of the eight guest rooms at The Court, or bring the whole family together in a cottage or home in town.

Spend the morning on the beach, the afternoon finding gifts and the evening back in Central Square. Whether it is your family’s first Christmas in Seaside or your tenth, there is always room for one more tradition.

More holiday events will be added to the Seaside events calendar as they are announced.

See the Seaside Events Calendar

Christmas in Seaside: Frequently Asked Questions

What is there to do for Christmas in Seaside, Florida?

The holiday season in Seaside begins with the Seaside Holiday Parade and Turn on the Town on Saturday, November 28, 2026. Throughout the season, visitors can shop for gifts in Seaside’s shops, gather for dinner at local restaurants and enjoy walks on the beach. More holiday events will be added to the Seaside events calendar as they are announced.

When is Turn on the Town in Seaside in 2026?

The Seaside Holiday Parade and Turn on the Town takes place on Saturday, November 28, 2026, from 3 to 8 PM at the Seaside Amphitheater in Central Square.

Where can I go holiday shopping in Seaside?

Seaside’s shops are all within walking distance in town, including The SEASIDE Style®, Kids + baby by The Seaside Style®, Headley Hat Co and Lala Links. Hours can vary by merchant, so it is a good idea to check ahead before your visit.

Where can I stay in Seaside for the holidays?

Seaside offers a range of places to stay, from The Court, a boutique hotel with eight guest rooms, to private cottages and homes available through Homeowner’s Collection and other rental partners.

Santa sitting on golden throne with two smiling, face-painted children at SEASIDE.

September 07, 2025

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Colorful lanterns, decorated Christmas tree & festive furniture create a cheerful vibrant holiday-themed restaurant interior.

HOLIDAYS DINING

Miracle Pop-up Bar Returns to Daytrader in Seaside

‘Tis the season! The famed Miracle Pop-Up Bar is set to return to Northwest Florida’s only location in Seaside, Florida, at The Daytrader for its third season. Opening Monday, November 17, Miracle at The Daytrader will bring over-the-top festive décor, whimsical holiday nostalgia, and inventive Christmas-themed cocktails to 30A’s beloved seaside escape.

The Miracle concept, born in 2014 in New York City, has since expanded to more than 200 locations worldwide across the United States, Canada, Europe, Asia, and Central America. Known for its dazzling decorations, kitschy cheer, and collectible holiday glassware, Miracle has become a global holiday tradition.

At The Daytrader—recently awarded Best Cocktail Spot on 30A in the 2025 Hot Spot Awards and helmed by James Beard Award semi-finalist Chef Nikhil Abuvala—guests can expect a tropical twist on the holidays. This year’s menu features new creations such as the Dancing Sugarplums and Miracle Mouse, joining returning fan favorites like the Christmapolitan, Snowball Old-Fashioned, and Jingle Balls Nog. Exclusive limited-edition glassware will also be available for purchase, including festive staples like the Santa’s Head, SanTaRex, and Christmas Unicorn, along with brand-new seasonal designs.

From November 17 through December 31, locals and holiday travelers alike can swing by Miracle at The Daytrader for a fully decked-out Christmas experience where tiki culture meets holiday kitsch. Guests can sip playful seasonal cocktails beneath a thatched roof, surrounded by twinkling lights and eccentric décor—a holiday mash-up only Miracle can deliver. The Daytrader is open daily from 11 AM – 9 PM, operating on a first-come, first-served basis.

As part of its global mission, Miracle will once again donate 10% of all proceeds from select glassware sales (including Santa Pants, Christmas Carol Barrel, and Santa Heads) to the Seva Foundation, a nonprofit dedicated to preventing blindness and restoring sight worldwide.

By Hannah Grace Abuvala

November 06, 2024

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