Your Fall Bucket List on Hilton Head Island

4. Book a public or private dolphin cruise. Hop on a skiff with Island Skiff Adventure Tours for an up-close and action-packed dolphin tour* this fall. Outside Hilton Head also offers Dolphin Eco Tours* as well as Sunset Dolphin Cruises* if you’re looking for a more laid-back and cozy experience as the weather starts to cool off. Vagabond Cruise offers similar tours* on a slightly larger boat with food and drink service, or, if you’re looking for a more exclusive outing, Cross Island Cruises offers private dolphin tours* and private sunset dolphin cruises*. Indulge in a private boat that is BYOB and dog-friendly, with a tour that is personalized to your group and interests!  *Seasonal. Check for availability.
5. Plan a romantic fall getaway. If sunset dolphin cruises and walks on the beach pique your interest, go all-in and plan an entirely romantic fall getaway with your significant other this autumn. Hilton Head Island is a dreamy destination in all seasons, but the quieter atmosphere, shorter days, and fall flavors make the autumn months perfect for a romantic vacation. Catch the sunrise from your hotel balcony or take a walk down to the beach for stunning sunrise views, followed by a day of peaceful bike rides and scenic trail walks, topped off with a sunset cruise or dinner by the water.
6. Order some oysters at one of our favorite seafood restaurants. Oyster season in the Lowcountry starts in September and lasts until April, so make sure you take advantage of the meatier and tastier flavor that the cooler weather brings to our local seafood. Some of our must-visit seafood restaurants include Poseidon’s The World is Your Oyster Raw Bar, Quarterdeck’s rooftop oyster bar, The Old Oyster Factory in Broad Creek, and Hudson’s Seafood House On The Docks.

7. Don’t miss the Hilton Head Island Oyster Festival. If you still haven’t gotten your fill of oysters and you happen to be visiting on November 7th and 8th, 2025, join us for Hilton Head Island’s Oyster Festival. On Friday, indulge in all-you-can-eat steamed local oysters, lowcountry boil, pulled pork, seafood chowder, and chili while you rock out to a live band. On Saturday, enjoy local artisan pop-up shops and live music.
8. Rent a bike and cycle the miles of scenic pathways around the island. There are nearly 30 bicycle rental shops on Hilton Head Island, so there’s something for novice and expert cyclists alike. Pedals Bicycles offers beach cruisers, mountain bikes, and road bikes, along with accessories like kiddie carts and child seats. LowSea Bike, Beach, and Baby Rental, Inc. offers cruisers, bikes, and trikes for all ages to get your family cycling trip off to the races. Peddling Pelican Bike Rentals, Inc. even offers delivery services to beaches and hotels in the area!
9. Play a round of golf at a championship course. Fall is the perfect time to tee off on Hilton Head Island. With open courses free of the crowds, you can easily get your preferred tee time, and the breezier weather means you can spend even longer out on the course. There’s really no better time to experience seaside golfing in the Lowcountry.

10. Partake in the Hilton Head Island Shrimp Festival. This must-attend event for shrimp lovers is hosted at The Sea Pines Resort in Harbour Town on September 20th, and features all-you-can-eat shrimp prepared by local chefs, craft beer, live music, specialty vendors, and activities for the kids. What more could you ask for?
11. Attend the Concours d’Elegance & Motoring Festival. If you’re a car enthusiast, look no further than the pinnacle of motoring experiences on Hilton Head Island: The Concours d’Elegance. The motoring festival takes place between October 29th and November 2nd, 2025, and features showcases, a film festival, a driving tour, and so much more. The Concours d’Elegance is the centrepiece of the event and celebrates the history, prestige, and innovation of the automobile.
12. Visit the Coastal Discovery Museum. The fall programming at The Coastal Discovery Museum is extensive and includes walking and kayaking tours, story times, classes, and educational wildlife talks. Learn about Gullah heritage, island stories, beaches, blue crabs, reptiles, and so much more during your visit to Hilton Head Island. 

13. Ignite your senses at the Lantern Parade. The annual Lantern Parade is one of the most beautiful displays you’ll see all fall on Hilton Head Island. The community comes together and alights hundreds of unique lanterns, sparking imagination and joy among visitors and locals alike. Make your own lantern and join the parade or simply delight in the spectacle before your eyes. See highlights from the 2024 parade to get your creative juices flowing.
14. Participate in the Annual Turkey Trot 5K. Yes, this is a race held on Thanksgiving, and yes, it has the best name ever! What better way to celebrate Thanksgiving — and to work up an appetite before the big meal — than coming together for a run? Register your friends and family for the 37th Annual Turkey Trot hosted by the Hilton Head Island Recreation Association, and be sure to bring some non-perishable donations to help their cause.
15. Catch the end of sea turtle season. Loggerhead sea turtle nesting season runs from May through October on Hilton Head Island, so there’s still time to catch a sighting of the little hatchlings emerging from their nests. This is one of those once-in-a-lifetime experiences, and absolutely worth the trip to try and glimpse a natural phenomenon with your own eyes. Learn more about sea turtle season in the Lowcountry here and follow along with updates from Sea Turtle Patrol Hilton Head Island so you don’t miss any breaking sea turtle news.

With the advent of fall festivals, activities, events, and a plethora of other things to do on Hilton Head Island this fall, you’ll have no problem filling your itinerary. But if you’re trying to check off everything on this bucket list, you’ll want to plan multiple visits to the Lowcountry to enjoy each of the exciting festivals and events. The fall months are approaching, and cooler weather, changing colors, and a jam-packed event season are on the horizon. It’s time to get planning! Request your free 2025 Vacation Planner today.