Don’t Miss These Ten October 2026 Events on Hilton Head!
Updated: 4 hours ago
Plan out your fun for the month with the Hilton Head October Events & Activities Guide. For even more Hilton Head Island happenings, check out This Week On Hilton Head's full Events Calendar. And stay tuned for our Halloween on Hilton Head Guide coming soon!
GULLAH FOOD FESTIVAL
Dive into a celebration of heritage with authentic Gullah cuisine, lively music, and engaging storytelling. Savor local dishes and discover the rich traditions that make Gullah culture unique. This festival is perfect for families, food lovers, and anyone eager to learn and enjoy.
October 17, 2026
DEAR EVAN HANSEN
Through October 25, 2026
Winner of six Tony Awards, Dear Evan Hansen is a profound contemporary musical for anyone who’s ever felt alone in a crowded room. When Evan fabricates a deep friendship with a deceased classmate, he finds himself caught in a whirlwind of events that thrusts him into the center of a grieving family’s life.
JEEP ISLAND MAIN EVENT & SLIDER SHOWDOWN
Enjoy the spectacular beauty of Hilton Head Island with fellow Jeep enthusiasts while sampling the area’s best sliders. The day will feature a Show and Shine, live music, slider tastings ($5 or under), food vendors, Pluck a Duck, kids zone, and more.
October 10, 2026
CRESCENDO
SONGWRITER SHOW
This free event features a night of original acoustic music and storytelling under the stars, highlighting regional talent over traditional cover songs. Local favorites Eric Reid & The Hebron Road Ramblers will headline the showcase, alongside guest performances by Matt Eckstine and Nick Poulin. Attendees are encouraged to bring lawn chairs or blankets and enjoy the on-site local food trucks, making it a suitable evening to experience the best of Hilton Head Island's 10th Annual Crescendo arts festival.
October 23, 2026
SYMPHONY
UNDER THE STARS
Get ready for a swinging celebration of the music of Harry Belafonte! Trinidad-born trumpeter, composer, and storyteller Etienne Charles and modern vocal icon René Marie, a two-time Grammy Award nominee, join Maestro John Morris Russell and the Hilton Head Symphony Orchestra for an evening filled with the rhythms, melodies, and spirit of the Caribbean.
October 16, 2026
ITALIAN HERITAGE FEST
The Italian Heritage Festival is a robust celebration of Italian culture with food and live entertainment. The crowd-pleasing grape stomping contest will return as will the popular pizza eating contest! The Festival will offer a full slate of activities for locals, visitors, and kids.
October 17, 2026
MITCHELVILLE FILM FESTIVAL
Historic Mitchelville Freedom Park invites you to Beyond the Game: Sports and Social Change, a two-day film series exploring the intersection of sports, leadership, influence and social change.
October 21-22, 2926
ROCK N' RIB FESTIVAL
This year features a one night only event with music by Cowboy Mouth and local legends Cranford Hollow. Plus, an all-you-can-eat BBQ from local and regional superstar pitmasters, Orchid Paulmeier (One Hot Mama’s & Food Network), Nick Fazio (Slowcountry BBQ), Lee Lucier (Local Pie), and More!
October 18, 2026
MAC & CHEESE FESTIVAL
This cheesy celebration will feature local restaurants serving up creative mac & cheese dishes. Plus craft beer, live music, a jumbotron with college football games and more!
October 24, 2026
HALLOWEEN AT COLIGNY
Get ready for an evening of trick-or-treating, costumes, family fun and plenty of Halloween spirit at Coligny Plaza. Little ghosts and goblins can trick-or-treat throughout Coligny, with shops and restaurants opening their doors to welcome families.