Experience 30A at The Pearl Hotel

Year-Round Special Events

At The Pearl Hotel, your getaway is more than just a luxurious stay—it’s a chance to dive into the dynamic spirit of South Walton’s 30A. Ideally situated in the charming Rosemary Beach® community on Scenic Highway 30A, The Pearl Hotel puts you right in the midst of a lively calendar of events all year long. After a day of local festivities, unwind and relax with a massage at Spa Pearl or savor a meal at our signature restaurant, Havana Beach Bar & Grill. For a unique dining experience, visit our rooftop venue with stunning views overlooking the Gulf and the town. Book your stay today and immerse yourself in the charm and excitement of 30A year-round.

Arrival

Departure

DISCOVER WATERSOUND® WEEKEND

October 2-4, 2026 | Watersound®

Explore the possibilities of coastal living during Discover Watersound® Weekend, a curated experience designed for those interested in learning more about Watersound's residential communities and the Northwest Florida lifestyle. Throughout the weekend, guests can tour select communities, connect with the Watersound team, and enjoy live music, special events and thoughtfully planned experiences that showcase the area's distinctive amenities and natural beauty. Stay at WaterColor Inn and enjoy 15% off standard rates.

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HARVEST WINE & FOOD FESTIVAL

October 15-18, 2026 | WaterColor®

The annual Harvest Wine & Food Festival by Destin Charity Wine Auction Foundation will provide patrons the opportunity to sip and savor some of the world’s finest wine and culinary selections while enjoying the iconic WaterColor beach town. Join fellow wine aficionados for four days of epicurean excellence.

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SEEING RED WINE FESTIVAL®

November 5-8, 2026 | Seaside®

The Seeing Red Wine Festival is a celebrated annual event featuring an array of wine tastings, culinary delights, and live music. Set in the charming town of Seaside®, this festival offers guests the opportunity to sample a wide selection of wines while enjoying the vibrant atmosphere of one of 30A’s most iconic beach towns.

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WATERCOLOR® MOUNTAINFILM ON TOUR

November 6-7, 2026 | WaterColor®

Celebrate the 26th Annual WaterColor Mountainfilm on Tour Festival with two days of extraordinary films created to inspire courage, thought and empathy. Enjoy this eclectic mix of captivating films that enhances the bold imagery of these remarkable stories in an outdoor setting with a starry backdrop to enhance the unfolding clips of thought-provoking films.

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ALYS BEACH CRAFTED

November 11-14, 2026 | Alys Beach

Alys Beach Crafted is an event designed to celebrate the collaboration of talents that enhance the 30A experience. Originating from the success of 2019’s Firkin Fête, this event focuses on showcasing crafted beverages, culinary experiences, artistry, and workmanship. Alys Beach will host a full linup of events, including Holiday Makers Market, Firkin Fête, Experiential Dinners, and the Spirited Soirée, where renowned craftspeople from across the country will share their skills and stories.

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ROSEMARY BEACH UNCORKED™

November 14, 2026 | Rosemary Beach®

Taste the very best of food and wine Rosemary Beach® has to offer. Savor exceptional food from the finest local restaurants, including Havana Beach Bar & Grill, explore a diverse selection of wine, and enjoy live music. Don’t miss this opportunity to indulge in a premier wine-tasting experience.

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30A 10K THANKSGIVING DAY RACE

November 26, 2026 | Rosemary Beach®

The 30A 10K, voted one of the top 10 turkey trots in the South, offers a flat, scenic route along 30A with views of South Walton's architecture and dune lakes. Runners of all ages can enjoy a DJ, local vendors, and a post-race celebration with breakfast, plus a complimentary Mimosa and Bloody Mary bar. Participants receive a commemorative race shirt and medal. With a 10K, 5K, and 1-mile run/walk, there's a race for everyone!

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30A SONGWRITERS FESTIVAL

January 15–18, 2027 | Festival Headquarters- WaterColor® | Performance @ Various South Walton Venues

Fans of great music are invited to enjoy the 18th Annual 30A Songwriters Festival over the four-day Martin Luther King Jr. holiday weekend. With an internationally prominent line-up of singer-songwriters and local artists, this festival is full of soulful melodies, powerful vocals, and compelling lyrics. Book your stay at The Pearl Hotel and enjoy more than 225+ performances from multiple venues along 30A.

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SEASIDE SCHOOL™ HALF MARATHON + 5K

February 11–14, 2027 | Seaside®

Every year, athletes from around the world meet up in Seaside, Florida, for Northwest Florida's signature running event and paramount fundraisers for SEASIDE SCHOOL™, the oldest public charter school in Florida. With lots of festivities throughout the weekend, including Taste of the Race, a culinary extravaganza celebrating local flavors and culinary masters, to the Race Expo, the race is a great way to reach your running goals and spend time with your friends and families in one of the most iconic beach communities in the world.

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DIGITAL GRAFFITI FESTIVAL

May 19–20, 2028 | Alys Beach

Experience the bi-annual Digital Graffiti, a captivating outdoor art festival where digital artists project original works onto the striking white walls of Alys Beach, transforming the town into a vibrant, immersive gallery. This internationally celebrated event invites artists and audiences alike to explore the dynamic fusion of art, architecture, and technology under the stars.

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