What to Do

May - The annual Hilton Head Island Boat Show held in the picturesque Windmill Harbour Yacht Basin. The Southeast’s Premier In-Water Boat Show, will feature over 60 beautiful boats from across the country. In addition, a variety of nautical lifestyle and marine services vendors will have booths setup around the harbour. Shop for clothing, jewelry, art, boating gear, kayaks, paddleboards and much more. The Boat Show will feature cuisine from the South Carolina Yacht Club, live entertainment, workshops and interactive displays.

February - The family friendly headlining event of the Wine and Food Festival, features area restaurants/chefs serving up seafood specialties and other tasty cuisine, a Kids Zone, new Artisan Market, Chef Cooking Demonstration Stage and more.

February - Join the Hilton Head Island Marathon, Half Marathon & 5K. This marathon features a scenic certified course that starts at Jarvis Park and takes participants through two parks and over the Broad Creek. A flat, fast course that is a prequalifier for the annual Boston Marathon in April. 

October - The Hilton Head Island Motoring Festival & Concours d’Elegance will include major international names in automotive collecting and racing. Events include a Club Car Showcase, Aero Expo, Concours D’Elegance, Savannah Speed Classic, Bluffton State of Mind Driving Tour, Flights and Fancy Aeroport Gala and the Hilton Head Auction.

November - The annual Oyster Festival highlights steamed, fried and stewed oysters along with other delicious food for non-oyster eaters! There will be live entertainment, kid zone, marshmallow roasting and Sports Lounge for those fall Football games! 

March - The Hilton Head Wine & Food Festival returns with a week full of events sure to please many all across the Lowcountry! South Carolina’s Premier Coastal Wine Competition & Culinary Event, the 31st annual Hilton Head Wine & Food Festival will not only feature spectacular celebrity chef showcases and intriguing wine education sessions, but also live entertainment and, of course, the famed Grand and Public Tastings.

Summer - Join in at the Sea Pines Forest Preserve every Thursday for an evening of Lowcountry activities, ghost stories and toasting marshmallows around a campfire. Reservations are required.

September - The best live local music combines with gourmet food and fantastic sunset water views weekly in the fall for the return of Music & Taste on the Harbour. Local bands will take the stage, while select Shelter Cove restaurants offer appetizers and drink specials. Entrance to the event is free and it is weather permitting.

December - Enjoy the New Year’s Eve Celebration in Harbour Town with two ball drops  the first at 7 p.m. and the second at midnight! Enjoy a fun and festive Harbour Town's New Year’s Eve, local dining and activities with their iconic lighted golf ball drop from the top of the Harbour Town Lighthouse! 

Summer - Each Thursday night, Parrot Palooza draws in crowds with island-themed music and entertainment designed for family fun. Beginning at 6 p.m., Parrot Palooza features entertainment, music, food, drinks and more. With the magnificent Shelter Cove sunset as a backdrop, Admission is free.

April - When the cheers are louder and the Southern hospitality is a few degrees warmer – it’s Island Time. That nowhere-else-on-earth time when the RBC Heritage comes to Hilton Head Island for some Golf! It’s the amped-up mood and carefree tone that lets you know Plaid Nation is in town for a week of events and has come to play.

October - Come enjoy the fall festivities and watch the exciting sailboat races at the Annual Harbour Town Cup Regatta on Saturday, and the Annual Calibogue Cup Regatta on Sunday. The regattas, showcased by fall events in Harbour Town, can be enjoyed by spectators from the piers of Harbour Town. 

December - Visit Santa’s Village at The Salty Dog Café in South Beach Marina Village to enjoy beautiful light displays, savor Christmas treats and write letters to send to the North Pole. There will be pictures with Santa.

April - The best live local music combines with gourmet food and fantastic sunset water views for the return of Music & Taste on the Harbour. Local bands will take the stage, weekly during the Spring with select Shelter Cove restaurants offering appetizers and drink specials.

March - The Annual Hilton Head Island St. Patrick’s Day Parade begins at Coligny Circle at 3 p.m. Every year, the parade is held the Sunday prior to St. Patrick's Day, or on St. Patrick's Day if it falls on a Sunday.