Festivals Worth Traveling For: Best Festivals on 30A

Image credit: 30A Songwriters Festival/Shelley Swanger

Life along Scenic Highway 30A is beautiful all year long—but when festival season hits, things really start to sparkle. Whether you’re a foodie, music lover, wine connoisseur, or just someone who loves an excuse to celebrate, 30A’s calendar is stacked with events worth planning a trip around.

Pro tip: Our festivals are very popular and often sell out quickly. Book your stay early with Grayt 30A Vacations, and we’ll help you find the perfect home base for your celebration-filled getaway.

Here’s your season-by-season guide to some of the most noteworthy festivals on 30A!

Winter Festivals

30A Songwriters Festival—Grayton Beach

Every January, hundreds of singer-songwriters turn 30A into one giant stage. Past lineups have included Grammy-winning songwriters alongside emerging artists, making the 30A Songwriters Festival a can’t-miss weekend for music lovers. Over 175 artists perform over the four-day weekend in venues along the 30A corridor, from large amphitheaters to local restaurants and bars.

Sandestin Gumbo Festival—Sandestin

The two-day Sandestin Gumbo Festival is one of the most beloved winter food events on the Emerald Coast. Held every February at the Village of Baytowne Wharf, the event kicks off with a seafood boil—picture steaming pots of shrimp, crab and corn shared at long, communal tables. Saturday brings everyone’s favorite—the popular gumbo cook-off where local restaurants compete for “Best Gumbo” bragging rights. You get to taste them all (and vote for your favorite).

Spring Festivals

30A Wine Festival—Alys Beach

This elegant, multi-day event in March celebrates fine wine and culinary artistry with a packed schedule of tastings, seminars, and chef-led dinners. The beloved “Bourbon, Beer & Butts” night pairs Southern barbecue with craft brews and top-shelf bourbons, while the Grand Tasting—set in the beautiful heart of Alys Beach—is the weekend’s crown jewel.

Sandestin Wine Festival—Sandestin

Nicknamed the “Kentucky Derby of Wine Festivals,” this April tradition at Baytowne Wharf features hundreds of wines paired with fresh Gulf Coast seafood and live entertainment. Guests enjoy strolling the waterfront, listening to live music, and meeting winemakers in a festive, relaxed atmosphere.

Digital Graffiti Festival—Alys Beach

In May, the white walls of Alys Beach transform into a living art gallery at the Digital Graffiti Festival. Artists from around the world project digital art animations onto buildings, courtyards, and pathways across town, turning the entire place into a glowing, walkable canvas. Music and gourmet food complete this one-of-a-kind immersive experience.

Summer Festivals & Fun

Summer Concert Series

From Seaside’s amphitheater to the lawns of Rosemary Beach, free weekly concerts pop up all along the coast. Pack a blanket, grab a drink, and enjoy live music under the stars.

Farmers Markets

From Seaside to Rosemary Beach, farmers markets run year-round but truly shine in summer with fresh local produce—from tomatoes to peaches—plus a selection of artisanal cheeses, local honey, handmade soaps, and local art.

Family Movie Night at The Big Chill

Enjoy a summer evening with the whole family at Family Movie Night at The Big Chill. Movies play on a 25-foot jumbotron and on TVs under the pavilions, so you’ll have a great view from anywhere. Come early to enjoy food, drinks, and yard games before the movie starts. Check The Big Chill website for the full schedule.

4th of July Celebrations

Red, white, and blue takes over 30A with parades, fireworks, and concerts in Seaside, Rosemary Beach, Grayton Beach, and beyond.

Fall Festivals

Harvest Wine & Food Festival—WaterColor

The Harvest Wine & Food Festival, hosted in WaterColor each October, is a four-day gourmet experience that is sure to delight both wine and culinary enthusiasts alike. Rated as one of the premier wine and food festivals in the Southeast, the Harvest Wine & Food Festival provides patrons the opportunity to sip and savor some of the world’s finest wine and culinary selections. Events range from intimate wine dinners to a Grand Tasting on the WaterColor Marina Park lawn.

Baytowne Beer Festival—Sandestin

If craft beer is your thing, we’ve got a festival just for you! Every October, Baytowne Wharf transforms into a craft beer lover’s paradise, with more than 40 brewers pouring nearly 200 unique beers to sample. Brewery reps lead engaging seminars on the art of lagers, ales, and everything in between, with plenty of live music to set the stage. Add in delicious food pairings and you’ve got the perfect fall weekend on the coast.

Bloody Mary Festival—Miramar Beach

The Market Ships in Miramar Beach kicks off fall with a creative twist on brunch. Restaurants compete to create the most over-the-top Bloody Mary, complete with garnishes that might include bacon, pickled okra, shrimp, or mini sliders.

Flutterby Arts Festival—Watersound Beach

This family-friendly event celebrates the annual Monarch butterfly migration with kids’ art activities, live music, lawn games, a butterfly parade, and hands-on workshops. It’s a joyful blend of art, nature, and community spirit.

Seeing Red Wine Festival—Seaside

For more than 30 years, this beloved tradition has invited wine enthusiasts to the coast to toast the finer things in life. Over four days each November, guests enjoy expertly curated wine dinners, educational seminars, and the Grand Tasting set against Seaside’s postcard-perfect backdrop. Named one of Fodor’s Travel’s “Top 10 Can’t-Miss Fall Wine Festivals,” Seeing Red is the ultimate 30A experience for wine lovers.

WaterColor Film Festival (Mountainfilm on Tour)—Santa Rosa Beach

Every November, this two-night outdoor film festival presents a hand-picked selection of inspiring documentaries from the renowned Telluride-based Mountainfilm Festival. Screenings take place under the stars at the WaterColor Marina Park Amphitheater in Santa Rosa Beach, showcasing powerful stories that explore cultures, protect the environment, and encourage adventure.