January 27, 2025Seaside. A beautiful beach town along 30A, it’s also a nonstop playground of fun, flavor, and festivities, January through December! From toe-tapping tunes to dachshund derbies, every season brings something unforgettable.
The lineup of events? Let’s look at why Seaside is a year-round hot spot for makin’ memories. A heads up: Clear your calendar now!
COZY UP TO WINTER.
🎶 30A SONGWRITERS FESTIVAL | JANUARY
Kick off the year with the soothing sounds of the 30A Songwriters Festival. This highly anticipated event features celebrated artists from across the country, creating a cozy and energetic atmosphere.
Seaside’s venues transform into intimate performance spaces, making it the perfect way to enjoy cooler days with live music. Bonus points if you’re sipping a hot cocoa while humming along.
🏃♀️ SEASIDE SCHOOL HALF MARATHON & 5K | FEBRUARY
Lace-up your sneakers and hit the scenic course for a good cause! This race weekend combines fitness, family fun, and fabulous food. The Seaside School Half Marathon & 5K is more than a race, it’s a weekend full of family-friendly activities, local food vendors, and plenty of post-run celebrations.
Whether you’re running, cheering, or just here for the post-race snacks, you’re part of something big. And yes, selfies with your medal are mandatory.
✨ THE NUTCRACKER BALLET | DECEMBER
When the holidays roll around, Ballet Pensacola brings magic to the Seaside Amphitheater with its stunning performance of The Nutcracker. This cherished tradition is a festive favorite that delights both locals and visitors.
Grab your coziest blanket and prepare for a magical evening under the stars. Pro tips: arrive early to snag the best spot for this enchanting show. And cookies and cocoa make it extra festive.
SPRING INTO AWESOMENESS.
🏆 SEASIDE PRIZE WEEKEND | FEBRUARY
Who knew urban design could be this exciting? Architecture and design enthusiasts, this one’s for you. The Seaside Prize Weekend, hosted by the Seaside Institute, celebrates excellence in urban design and honors innovators who shape how communities connect and thrive. It’s like a TED Talk, but with way better scenery.
🐰 EASTER EXTRAVAGANZA | APRIL
Seaside pulls out all the stops on Easter. Families can enjoy egg hunts, live entertainment, and creative crafts—all set against the backdrop of Central Square’s lively charm. There’s even a chance the Easter Bunny might make a cameo, so bring your camera.
🌹 SLEEPING BEAUTY BALLET | APRIL
Another stunning performance by Ballet Pensacola, Sleeping Beauty enchants audiences at the open-air Seaside Amphitheater. It’s a cultural gem that makes spring evenings in Seaside even more magical. And yes, it’s perfectly acceptable to hum “Once Upon a Dream” all the way home. Bring a picnic, your favorite people, and prepare to be enchanted.
WHEN SUMMER SIZZLES.
🎭 CHILDREN’S THEATER PERFORMANCES | MARCH–AUGUST
Bring the little ones for delightful productions by the REP Theatre at the Seaside Amphitheater. Little ones will love these productions, which combine engaging storytelling with the joy of outdoor entertainment. Cue giggles and happy applause from the pint-sized crowd. Expect a few rounds of “Can we watch it again?”
🎥 CENTRAL SQUARE CINEMA | MARCH–OCTOBER
Enjoy a starry outdoor movie night at the Amphitheater, which continues to be the heart of Seaside. Grab a blanket, some popcorn, and your favorite people for a relaxed evening of movie magic in Central Square Cinema. A family favorite!
🎶 LABOR DAY WEEKEND CONCERT | AUGUST
As summer comes to a close, Seaside knows how to bid farewell to another season of sunshine. The Labor Day Weekend Concert fills the town with live music and a festive vibe that captures the essence of summer on 30A. It’s the ultimate encore to a season of sunshine and smiles: Beachwear optional, good vibes required.
FALL INTO FANTASTIC.
🍷 SEEING RED WINE FESTIVAL | NOVEMBER
Sip, savor, and mingle at this sophisticated wine fest. The Seeing Red Wine Festival is a sophisticated celebration of curated vintage wines paired with gourmet bites. It’s the ideal way to savor fall flavors and connect with fellow enthusiasts. Warning: you’ll leave with a refined palate and maybe a new favorite wine or three. It’s the grown-up getaway you deserve.
🐶 HALLOWEENER DERBY | OCTOBER
This quirky event features dachshunds racing for glory, paired with Oktoberfest-inspired activities. Halloweener Derby is a unique, family-friendly experience that’s just as fun as it sounds. If you’ve never cheered on a tiny dog in a costume, now’s your chance.
🎃 HALLOWEEN SPOOK-TACULAR | OCTOBER
From Trick-or-Treating around Seaside to a Halloween-themed movie night at Central Square Cinema, October in Seaside delivers all the spooky vibes and festive fun you could want. Grab your ghostly getup and join the fun. Creepy or cute, there’s always a bit of friendly competition.
ALL HOLIDAY, NO HUMBUG!
🕯️ CHRISTMAS EVE AT THE CHAPEL | DECEMBER
The Chapel at Seaside offers a peaceful escape with its Christmas Eve Chapel Services. The warm glow of candlelight and the serene setting make it a meaningful way to celebrate the season. With a nice mix of tradition, tranquility, and small-town charm, it’s pure holiday magic. Minus the stress of tangled lights.
🎉 NEW YEAR’S EVE BASH | DECEMBER
Ring in the new year Seaside-style with live music, dancing, and plenty of good cheer. Seaside knows how to throw a party! This community celebration sets the tone for an amazing year ahead. Fireworks optional, fun guaranteed, it’s the perfect way to kickstart your resolutions, or delay them for another day.
YEAR-ROUND JOY IN SEASIDE
From winter melodies to summer sunsets, no matter the season, Seaside knows how to celebrate life, capturing the heart of 30A’s culture and community. Ready to experience it all? Pair your event-filled adventure with a stay in one of Oversee’s luxurious vacation homes.
Seaside
Seamless booking, impeccable hospitality, and front-row access to the best of Seaside await. We’ll help make your trip unforgettable. See you in Seaside!
Your friends at Oversee.
