Kayaking at Dawn

Four Hilton Head Island Weekend Trips You Can’t Miss This Fall

Warm weather, picture-perfect sunsets, and an events calendar that’s jam-packed with something for everyone: there are plenty of reasons why fall is one of the nicest times to plan a visit to Hilton Head Island! During the fall months, the pace here in Lowcountry is a little more laid-back and relaxed, so you can take your time exploring America’s Favorite Island (for four years in a row!) Convenient flights to the nearby Savannah/Hilton Head International Airport make it easier than ever to experience “Island time”. And with some of our biggest and best events happening at this time of year, you’ll be able to take in some world-class entertainment, too! 

From a collection of some of the world’s finest cars to a delectable seafood feast, here are five ways to spend a weekend on Hilton Head Island and in Bluffton this fall.

For a five-star weekend


old car

What: Hilton Head Island Motoring Festival & Concours d'Elegance

When: November 1-3

Where: Around Hilton Head Island (Port Royal Golf Club, Bluffton and the Hilton Head Island Airport) 

Looking for a taste of the finer things in life this fall? One of Hilton Head Island’s premier annual attractions, the Hilton Head Motoring Festival & Concours d’Elegance is a luxurious celebration of automobiles, racing, fine dining, and more. 

Stroll through the Flights & Fancy Aeroport Gala on November 1, where vintage aircraft will be on display alongside pristine Concours cars. On Saturday, November 2, the Design Among the Stars event at the Harbour Town Clubhouse gives guests an opportunity to mingle and dine with some of the top automotive designers in the world. Bid on automotive art that’s sketched before your very eyes! 

The weekend’s festivities wrap up with the Concours d’Elegance on Sunday, November 3, when nearly 75 judges will review more than 200 classic cars and choose the 2019 Best in Show.  

For (sea)foodies



What: Bluffton Arts and Seafood Festival

When: October 12 – 20, 2019

Where: Bluffton

When you visit eclectic Bluffton this October, be sure to pack your appetite! The 15th annual Historic Bluffton Arts and Seafood Festival is a week-long celebration of food, art, and culture–the perfect treat for all the senses–served with a generous dash of warm Southern hospitality! 

Take some time to browse Streetfest, where you can peruse the works of more than 100 artists displaying and selling their art while sampling delicious food featuring fresh local ingredients. Tap your toes to great musical entertainment and soak up Bluffton’s charming vibes. 

For drama queens (and kings) 

What: Crescendo

When: October 10-November 15

Where: Hilton Head Island (various locations)

Whether you’re craving a little dramatic flair or want to take a step back in time, Crescendo is the perfect festival for getting your arts, culture, and history fix on Hilton Head Island. Museum and gallery exhibits, theatrical productions, concerts, guided historical tours, poetry readings, dance performances–more than 75 unique offerings are expected to attract 65,000 visitors during the festival’s month-long schedule. 

Test your own artistic ability with a hands-on arts experience, or immerse yourself in Lowcountry history and culture. Crescendo is a wonderful opportunity to discover the best of South Carolina’s arts scene while savoring Hilton Head Island’s hospitality, cuisine, and natural beauty.

For active adventurers

There are more awesome outdoor activities to do on Hilton Head Island than you could fit into just one weekend—but if that’s all the time you have, here are some of our favorites. With 33 courses in the area, golf is a definite go-to around here. If you’re getting in on Friday, take a swing at Harbour Town Golf Links and catch a stunning sunset by the iconic lighthouse. With courses by world-renowned architects like Robert Trent Jones Sr., Pete Dye, Davis Love III and Jack Nicklaus, you’ll be spoiled for choice on and around the island.

Hilton Head Island is also home to eight of the world’s top 100 tennis resorts and camps, and these aren’t any old courts. Perfect your serve surrounded by centuries-old oaks, tranquil tidal creeks, and incredible maritime forests. Want to get a little more of the great outdoors on Saturday? Get out on the water with a variety of aquatic activities. Kayak or paddleboard along beautiful waterways and keep an eye out for the island’s diverse wildlife, set out on a fishing expedition, or kick it up a notch with jet skiing, parasailing, surfing and more. Before you depart on Sunday, squeeze in a bike ride along the beach for the quintessential Hilton Head experience and snap some shots that are sure to up your Instagram game.


For family-friendly fun

walking on the boardwalk

Follow this itinerary. It’s no secret Hilton Head Island is one of the country’s top destinations for fun family getaways. If you’ve only got the weekend to spend, there are lots of awesome activities to make the most of your time on our island. Up for a swashbuckling adventure? Board a pirate ship and set off in search of hidden treasure. Young buccaneers will receive their own pirate name, face paint, temporary tattoos, and some loot to take home.

Spend Saturday surrounded by nature at the Coastal Discovery Museum. Set on 68 acres, explore nature trails, gardens, and a butterfly enclosure. Kick it old school at the Kids Zone by dressing up in costumes from Colonial days and learning about the culture and history of the island. Your kids will be having so much fun; they won’t even realize it’s so educational! Before you have to head out on Sunday, spend a low-key morning at one of our beautiful beaches. Build some sand castles, play in the surf, and enjoy some real quality family time.

Experience America’s Favorite Island this fall. 

Searching for even more things to see and do on Hilton Head Island this fall? Take a look at all of the great, upcoming events and happenings on our event calendar (the Connect Calendar), and start planning your perfect weekend getaway.

Kayaking at dawn

Find Your Island Time

Hilton Head is America’s favorite island, offering 12 miles of pristine beaches and everything you need for the ultimate retreat. Enjoy easy days relaxing in the sun, sand and surf on some of the best beaches in the country.
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