Summer has just about come to an end, and you might feel like your vacation options are limited. If all you want to do is lie on the beach, you might be right. However, if a vacation to you is about taking it all in—the arts, sporting events, festivals, and more—then you could be having fun on Hilton Head Island.


The first thing that comes to your mind when you think of Hilton Head is probably golf. Even though golf is mostly considered a summer sport, you can still find a few tournaments in the fall. In September, you’ll find the 21st Annual Hilton Head Regional Habitat for Humanity 2018 Golf Tournament & Auction or the NOC Annual Fore the Teachers Golf Tournament. While in November, you can see the Reilley’s Mortgage Network Match Play Championship.

If golf isn’t your thing, you can always try Pedal Hilton Head Island, 2018 in November or the Old Town Oyster 10k Road Race & 5K Fun Run in late October.


Hilton Head is about much more than just sports, though. Art and music are abundant in the fall. Jazz or Blues fan? Especially from the swing era? This is a great time to come to Hilton Head to see Legendary Bluesman Earl Williams or a tribute to Natalie Cole with Candace Woodson. Later in the season, you can catch Jazz – The Ulysses Owens Quartet or Deana Martin sings the music of her Father, Dean Martin.

If traditional art exhibits are what you’re looking for, you’ll find plenty of those on the island this Fall too. Come out to see Got Art  or the 2018 Public Art Exhibition on Hilton Head Island. Later in the season, you’ll still be comfortable outside, taking in the Chalk the Walk Live Street Art Competition. Prefer theater? Don’t miss Lean Ensemble Theater presents Shakespeare’s “The Tempest”.

Special Events

But there’s still even more to experience in Hilton Head. Summer comes to an end with the Harbour Town Fall Fest late in September. Later on in November, you can attend the Fall Festival or Out of the Darkness Walk. You can still enjoy your favorite parts of the autumn season here with the Caramel Apple Festival or Halloween on the Harbour.

One of the most notable events on the island is the Hilton Head Island Concours d’Elegance & Motoring Festival  in early November. Don’t miss it if you love classic cars.

So, whether you are coming to Hilton Head Island this fall for the traditional golf outings or you want to experience autumn’s traditions in an unconventional setting; if you want to come and hear some jazz or see some beautiful art, you’re bound to find something for everyone. Be sure to travel in style on the island while you’re here so you can see everything! Book your bicycle and other equipment rentals now so you can rest easy knowing your plans are covered.