October along Florida’s Scenic Highway 30A and the Emerald Coast is packed with festivals, live music, art shows, and family-friendly fun. From rare luxury cars showcased in Alys Beach at Cars of 30A, to the creative flair of the Grayton Beach Art Fest, and the toe-tapping performances at the inaugural Destin Songwriter Festival, the month is filled with unforgettable experiences. Food and drink lovers can sip their way through the Baytowne Beer Fest in Sandestin or the 10th Annual Bloody Mary Festival in Miramar Beach, while families can enjoy community favorites like the Halloweener Derby in Seaside and festive Halloween celebrations across the coast. Whether you’re a local or visiting, October is the perfect time to explore the beauty, culture, and community spirit of 30A and the Emerald Coast!
FEATURED EVENTS
Cars of 30A at Alys Beach
October 3rd- 4th, 2025
Alys Beach
Alys Beach sets the stage for two unforgettable days showcasing a curated collection of rare and high-performance automobiles. Against the backdrop of the town’s iconic white masonry and cobblestone streets, this celebration blends architectural beauty with automotive excellence!
Grayton Beach Art Fest
October 4th, 2025
Shacks Art | Grayton Beach
Shacks is hosting its first-ever Fall Art Fest, bringing together more than 100 artists indoors and outdoors for a full day of creativity. Guests can enjoy live music, kids’ crafts, and food and drinks from Grayton Corner Café while browsing an incredible variety of artwork. Sponsored by 30A Local Real Estate and Barker Williams Attorneys at Law, this community celebration promises art, entertainment, and fun for all ages!
Destin Songwriter Festival
October 10th-11th, 2025
Destin Harbor | Destin
The inaugural Destin Songwriter Festival brings acclaimed songwriters from across the country to the Emerald Coast for two days of unforgettable performances. Guests can enjoy free daytime shows on multiple side stages around the harbor, then head to the main stage in the evening for ticketed performances featuring the stories and songs behind the hits. Proceeds benefit Operation Song, supporting the military community!
The Market Shops 10th Annual Bloody Mary Festival
October 11th, 2025
The Market Shops | Miramar Beach
The Market Shops’ 10th Annual Bloody Mary Festival returns, benefiting Habitat for Humanity – Walton County. Guests will enjoy unlimited tastes of creative bloody marys crafted with Distillery 98’s Half Shell Vodka, plus food, shopping, live music, football, and more. A panel of judges and attendees will crown winners for the most delicious and creative creations!
Baytowne Beer Fest
October 11th, 2025
Baytowne Wharf | Sandestin
The Baytowne Beer Festival brings the ultimate craft beer experience to Sandestin with more than 150 domestic and international brews to sample, plus live music from The Typos and plenty of food to enjoy. Guests can explore Seltzer Lane, discover local favorites at Beer From Around Here, and taste international selections at Import Lane. With exclusive perks available through the Baytowne Pour Pass, this annual festival is a must for beer lovers!
Artisan Market at The Stalls on 30A
October 12th, 2025
The Stalls | Blue Mountain Beach
The Stalls will host a vibrant marketplace featuring more than 30 makers, artisans, and vendors from across the Southeast. Guests can browse jewelry, clothing, art, home goods, baked treats, and more, while enjoying food and drinks from Cowgirl Kitchen Market and Boxcar Annie!
Watersound Origins Porchfest
October 12th, 2025
Watersound Origins | Watersound
Porchfest returns to the Watersound Origins community for an afternoon of live music on porches and lawns, featuring performances by Nate Kelly, Sammi Accola, Gage Cowart Band, Casi Joy, and headliner The Caitlin Cannon Band. Guests can enjoy bites from local food trucks, relax with friends and neighbors, and soak in the family-friendly atmosphere. This free community event promises a day of great music, delicious food, and good vibes!
30th Annual Festival of the Arts
October 25th, 2025
Mattie Kelly Arts Foundation | Destin
The Mattie Kelly Arts Foundation will celebrate the 30th Annual Festival of the Arts with a vibrant, family-friendly weekend filled with art, music, food, and community. Guests can browse works from more than 100 juried artists, enjoy live performances, watch artist demonstrations, and take part in hands-on activities for all ages. The festival also features a food truck courtyard, beer and wine garden, and the popular People’s Choice Award. Free and open to the public, the event supports MKAF’s mission to inspire and enhance lives through arts and culture.
Luke Combs Bootleggers Bonfire
October 23rd-25th, 2025
Seascape Resort | Miramar Beach
Bootleggers Bonfire returns for its second year with an unforgettable weekend of music and memories. The lineup features Luke Combs with two unique sets, plus performances from The Castellows, David Lee Murphy, Dylan Marlowe, Ella Langley, and more. Guests will also enjoy special experiences like Whiskey Jam, The Wildcards 90’s Night, Songwriters Bonfire, Luke-I-Oke, and curated daily activities—all set against a laid-back coastal backdrop!
15th Annual Halloweener Derby
October 25th, 2025
Seaside Amphitheater | Seaside
The 15th Annual Halloweener Derby and Dog Costume Contest returns to the Seaside Amphitheater this fall. Guests can enjoy a festive day of four-legged fun as speedy dachshunds race for glory and pups of all kinds show off their most creative costumes. This beloved community tradition brings together families, friends, and dog lovers for a howling good time!
Halloween in SEASIDE
October 31st, 2025
Seaside Square | Scenic Hwy 30A
Seaside transforms into the Emerald City this Halloween with its annual Trick-or-Treat celebration. Families are invited to follow the Yellow Brick Road through Central Square, collect sweets from local merchants, and meet beloved Wizard of Oz characters along the way. The evening concludes with an outdoor screening of the classic film under the stars, making it a magical night for kids and kids-at-heart. Costumes are encouraged!
Halloween on the Boolevard
October 31st, 2025
Grand Boulevard | Miramar Beach
Grand Boulevard invites families to enjoy a festive evening of Trick-or-Treating with participating merchants. This free community event offers a fun and safe way to celebrate Halloween while exploring the shops along the boulevard!