2026 Hilton Head Island Events Guide: Top Festivals & Celebrations

By Hilton Head Insider

Hilton Head Island knows how to throw a celebration — and in 2026, the calendar is packed with unforgettable events. From seafood feasts under the stars and PGA golf tournaments to glowing beach parades and soulful cultural festivals, there’s something here for every kind of traveler.

Whether it’s your first visit or a return trip to America’s Favorite Island®, here are the must-experience events to plan your year around.

Celebrate Gullah Culture on Hilton Head Island (February 1–February 28, 2026)

What better way to welcome Hilton Head Island’s winter mild than with events that honor deep roots and community spirit? The Hilton Head Island Gullah Celebration invites locals and visitors alike to explore the vibrant traditions, food, music, and stories of the Gullah people. Recognized as a Top 20 Southeast event by the Southeast Tourism Society, this yearly gathering is an opportunity to learn more about an important part of the Lowcountry’s history and celebrate a living legacy that still shapes the region today.

Insider Tip: Don’t miss the family-friendly Gullah Market at Historic Mitchelville Freedom Park, where the scent of Lowcountry cooking pairs perfectly with Gullah art and culture.

Lowcountry Flavors at the Hilton Head Island Seafood Festival (February 23–March 1, 2026)

This celebrated gathering offers a full week of authentic Lowcountry flavor. From intimate wine dinners and dockside tastings to culinary demos by celebrity chefs, the 2026 Hilton Head Island Seafood Festival offers freshly caught, flame-seared, and artfully plated coastal bounty.

Insider Tip: Be sure to watch for fire pit feasts, mixology experiences, and the Tasting Tent event on Saturday.

Spring Sips at the Hilton Head Wine & Food Festival (March 22– March 28, 2026)

For over 40 years, the Hilton Head Island Wine & Food Festival has brought wine lovers, sommeliers, and foodies together to enjoy top-tier wines, Lowcountry bites, and creative pairings from top chefs nationwide.

Insider Tip: The Public Tasting event (March 28) is a favorite for good reason, with hundreds of wines, shaded tents, and live music all in one place.

RBC Heritage Presented by Boeing: PGA TOUR Excitement at Harbour Town (April 13–19, 2026)

A beloved Hilton Head tradition and one of only eight PGA TOUR Signature Events, the RBC Heritage Presented by Boeing takes place at Harbour Town Golf Links. This is more than a tournament. It’s a weeklong island celebration. Expect Plaid Nation to be out in full force, with top-ranked players, thrilling rounds, and Southern charm at its finest.

Insider Tip: Book early. Lodging fills fast this time of year. Explore where to stay.

wine and food festival, person pouring wine

Pedal Hilton Head Island: Scenic Rides for a Good Cause (May 3, 2026)

A feel-good, do-good event, Pedal Hilton Head Island takes riders through our bike-friendly trails — from beachside paths to shaded greenways. Expect ocean breezes, shaded trails, and plenty of smiling riders. With five distances for all levels of riders, plus a family fun ride, casual cyclists and passionate pedalers alike will find something to enjoy, with all proceeds supporting the Boys & Girls Club of Hilton Head Island.

HarbourFest at Shelter Cove: Weekly Summer Fireworks & Family Fun (June–August 2026)

One of Hilton Head Island’s most popular summer events, HarbourFest at Shelter Cove is a weekly celebration featuring live entertainment and family activities from June through August. Expect fireworks over the water and cotton candy smiles every Tuesday night all summer long. Plus, you’ll find arts and crafts booths, entertainers on the lawn, and waterfront dining that’s worth indulging in.

Crescendo: A Celebration of Arts, Culture & Community (October–November 2026)

Crescendo is Hilton Head Island’s signature fall arts festival, taking place in settings and venues across Hilton Head Island. Throughout October and November, you’ll enjoy theatre, dance, music, visual art, and literature — with events ranging from intimate gallery shows to full-scale performances.

Insider Tip: The Lantern Parade — an annual glowing procession down the beach that brings creativity and community together — is a must-do Crescendo event.

Concours d’Elegance & Motoring Festival: Classic Cars with Coastal Style (November 2026)

Fans of classic cars rejoice in November when the Hilton Head Island Concours d'Elegance & Motoring Festival rolls into town. Concours d’Elegance means “competition of elegance”, a fitting name for this exhibition of craftsmanship, design, and history. Events include a Club Car Showcase, a Rolls-Royce Owners' Club National Mini Meet, and the grand finale: the Concours d'Elegance. Seventy-five judges will select the Best in Show from over 200 spectacularly rare pre-1974 vehicles.

Plan Your Hilton Head Vacation Around 2026 Events

For couples, families, and solo travelers alike, Hilton Head Island’s 2026 event calendar offers something unforgettable — from fireworks and food festivals to cultural celebrations and classic cars.

Hilton Head Island’s 2026 calendar is already filling up, and so are hotel rooms, vacation rentals, and dinner reservations. If your heart is set on a specific event, book early, especially for spring and summer weekends.

Want help planning? Order your Hilton Head Island Vacation Planner or explore our featured travel offers to help map out your stay.