Posted on 8/31/2021


Summer may not truly be endless, but it can feel like it is on Hilton Head Island. We can’t promise piles of leaves to jump in [or rake for that matter], but we can offer plenty of waves to jump in and warm sunshine to soak up. Ocean temps are still enjoyable for swimming, and nights were made for making fireside memories.

Hilton Head is pretty much perfection in the fall! And the island has plenty to offer as far as fun and festivities. Here are a variety of some of the top happenings: 

Hilton Head Island Wine & Food Festival 9/14 – 9/18/21

Cheers! Wine and food enthusiasts raise their collective glasses to a week-long party celebrating the fruits of global wine partnerships, signature Lowcountry cuisine, grassroots cultural happenings, and the authentic fabric of a unique community.

Foodies and wine lovers come from far and wide to be a part of an inspiring series of events. Come celebrate our 35th anniversary of this annual Hilton Head Island rite of passage. Experience for yourself this year’s schedule of events including spectacular celebrity chef showcases, intriguing wine education sessions, live entertainment, and of course the famed Grand and Public Tasting events.

Italian Heritage Festival 10/23/21

Ciao!! This much-loved festival will be back for 2021 at The Coastal Discovery Museum at Honey Horn.

As always, the festival is a robust celebration of Italian culture and food. There’s also live entertainment, and if the music doesn’t get you moving our famous grape stomping contest sure will. They’ll be some new events too so don't miss it! The festival will offer a full slate of activities for locals and visitors alike.

A number of booths will be dedicated to traditional Italian foods, such as cheeses, breads, pasta, fish, meatballs, sausage and calzones, and delicious sweets, including Italian ice, gelato, biscotti and zeppoles – many sponsored by local restaurants. There’s something delicious for everyone’s taste, and there’s even a pizza-eating contest. All we can say to that is, “Mangia!!!”

Flights & Fancy Aeroport Gala 11/5/21

The now-iconic 19th annual Hilton Head Island Concours d'Elegance & Motoring Festival gets off to a flying start at the Hilton Head Island Airport the last Friday night in October.

Remarkable vintage aircraft descend on the island from across the country to show under the stars alongside pristine Concours cars. Guests will dine on the finest food Hilton Head Island has to offer and drinks will be flowing as the legacies of automotive and aviation come together for an unforgettable night!

Then on Sunday, November 7th over 200 cars and motorcycles will take to the 1st and 18th fairways of Port Royal Golf Club's Planter's Row Golf Course on the final day of the festival–but only one can be crowned Best of Show.

HHI Oyster Festival Weekend 11/12 – 11/13/21

Family fun on the half shell! Join us for a two-day seafood celebration at the new Lowcountry Celebration Park in Coligny Beach. Dive into all-you-can-eat steamed local oysters, Lowcountry boil, pulled pork, seafood chowder & chili [drinks sold separately]. Plus, there will be live music, a football viewing area, and a wine pull!

This fall, leave the raking behind and escape to Hilton Head Island. And nobody can help you plan the perfect island getaway better than we can at The Vacation Company. Our team has over 150 years of combined experience. Reach out today to one of our Hilton Head Island getaway specialists, and they’ll help you choose from our portfolio of nearly 400 exclusive Hilton Head Island vacation rentals. From breathtaking oceanfront estates to well-appointed golf course villas we bring you only the best Hilton Head Island has to offer.

Check out our vacation properties to make your plans now or call one of our reservation specialists at 1-843-686-6100.

Previous A FEW LOCALS' PICKS FOR HILTON HEAD ISLAND'S BEST VIEWS Carving Time for Family on Hilton Head Island in October Next