The fall season may not necessarily look the same on the island as it does in other locations known for colorful fall foliage, but once the leaves begin to change across the country, Hilton Head Island’s festival season starts ramping up. Starting as early as September, festivals and events start filling up the calendar, only adding to the fun for visitors on vacation. If one thing is true about the island, is that we love celebrating food: seafood, Italian food, BBQ, shrimp, oysters…we can go on and on about the delicious plates that will be served up by local and award-winning chefs over the next coming months. Almost every event will feature amazing musicians and live entertainment, as well as offer collections of local vendors and specialty pop-up shops. The island’s Pumpkin Patch will even be popping up in October. Read on to learn more about some of the major events happening on Hilton Head this fall.
September
End of Summer 5K
September 5, 2026
9:00am at Coligny Beach
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Celebrate the unofficial end of summer with the Hilton Head End of Summer 5K Run and Walk on September 5th, 2026. Starting and finishing at Coligny Beach, this family-friendly event welcomes participants of all ages for a scenic race along the island’s south-end shoreline. A portion of the proceeds benefits the Heritage Academy College Scholarship, making it a fun way to give back while enjoying one of Hilton Head’s most beautiful beaches. Participants can also earn custom awards, and the first 300 registrants will receive a commemorative race shirt.
Hilton Head Island Jam 2025 LOCASH Golf Bash
September 17, 2026
7:30am Registration, 8:30am Shotgun Start at Atlantic Dunes
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Join LOCASH for an unforgettable day on the green during HHIJ 2026, set against the backdrop of Hilton Head’s picturesque Atlantic Dunes Course at Sea Pines Resort. This exclusive tournament blends the thrill of music with the passion for golf, offering fans a unique way to connect with their favorite artists in the heart of a golfing paradise. This event benefits the Tunnel to Towers Foundation.
Island Jam 2026 Songwriter Festival
September 17-20, 2026
Various Locations
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Welcome back to the 4th Annual Hilton Head Island Jam, where Nashville’s songwriting brilliance meets Hilton Head’s charm–and it’s free to attend! Join us for music and storytelling in our picturesque Lowcountry settings. Featuring renowned, hit songwriters and emerging artists, the festival promises an intimate celebration of creativity and camaraderie.
Get ready for a lineup of events set across multiple iconic venues, including the serene Liberty Oak and the vibrant Lowcountry Celebration Park. For a full list of artists attending, to stay up to date with this year’s events, or even to take a look at last year’s inaugural festival, visit Island Jam’s website.
Hilton Head Island Shrimp Festival
September 19, 2026
1:00-4:00pm at Harbour Town
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The 8th Annual Hilton Head Island Shrimp Festival returns to The Sea Pines Resort on September 19th, 2026, serving up an afternoon of Lowcountry flavor and family fun. Sample creative shrimp dishes from more than 15 local chefs, enjoy tastings from regional craft breweries, browse specialty vendors, and listen to live performances from Nashville songwriters as part of the Hilton Head Island Jam Songwriters Festival. Families can also enjoy the Kid Zone with games, crafts, and activities, while guests vote for the People’s Choice awards for Best Dish and Best Brewery.
October
Rhythm & Brews
October 3, 2026
VIP Admission: 10:30am, General Admission: 11:30am at Shelter Cove Park
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Presented by the Hilton Head Island Wine & Food Festival (March 25-April 4, 2027), this year’s Rhythm & Brews will be held at the beautiful, Shelter Cove Community Park. With a general admission ticket, festival guests will be able to enjoy live music by headliner, Exit 8, as well has having access to purchase food from local vendors and unlimited tastings from over 100 breweries, distilleries, and wineries. A foodies dream, skip your lunch or dinner plans and spend your Saturday afternoon among friends and family in the Carolina sunshine with a stunning view of Broad Creek. All attendees must be 21 and over–no exceptions. Children and pets are not permitted.
This event is a participant in Ales for ALS, a program that raises money for vital ALS research at the ALS Therapy Development Institute.
Lowcountry Fish & Grits Music Festival
October 3, 2026
12:00pm at Lowcountry Celebration Park
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This is a can’t-miss experience that highlights the rich Gullah Geechee culture with delicious food, live music, and entertainment. The Lowcountry Fish & Grits Music Festival is great for all ages and will feature a mix of folk, funk, jazz, spoken word, R&B, and more. The on-site market will include many vendors selling culturally relevant clothing, art, and various other merchandise. Food vendors will offer an array of delicious hot, cold, sweet, and savory items that will leave you wanting to go back for more!
Jeep Island
Meet & Greet: October 9, 2026
5:00-7:00pm at Lincoln and South Brewing Company
Main Event: October 10, 2026
12:00-3:00pm at Lowcountry Celebration Park
After Party: October 10, 2026
3:00-7:00pm at The Bank
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A fundraiser that helps build the Island Recreation Association’s Children Scholarship, Jeep Island is a fun way for Jeep enthusiasts to gather together, show off their rides, have the chance to win a Jeep Wrangler, and more! Jeep Island Entry is $50 (for one Jeep and two people), includes access to Friday night’s Meet & Greet, Saturday’s Jeep Island & Chili Cook Off, afterparty, and a goodie bag. This year the event has a new addition: the Slider Showdown! More than 12 local restaurants will be serving sliders for $5 or less.
Italian Heritage Festival
October 17, 2026
11:00am-4:00pm at The Coastal Discovery Museum at Honey Horn
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A celebration of Italian culture, the 15th Annual Italian Heritage Festival will be held on the beautiful grounds of Honey Horn. The festival lineup will feature traditional Italian foods ranging from cheeses, breads, pasta, gelato, biscotti and more, so arrive hungry! There are scheduled activities for all ages, and of course, we couldn’t leave out the yearly Pizza Eating Contest! Parking on-site is free of charge. This event is rain or shine!
Pumpkin Patch
October 23, 2026
4:00-7:00pm
Shelter Cove Community Park
All are welcome to this complimentary event hosted by the Island Recreation Association. This annual event features a field of pumpkins to choose from, as well as the highly anticipated Kid’s Halloween Costume Contest that begins at 5:45pm.
Along with pumpkins, there will be bounce houses and other games. Train rides, concessions, and chances at climbing the rock wall will be sold individually. Explore the shops and have lunch or dinner at one of the many restaurants within the Shelter Cove Towne Centre.
Concours d’Elegance & Motoring Festival
October 29-November 1, 2026
Various Locations
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Since 2002, the Concours d’Elegance has been celebrated in the Lowcountry. Celebrate the art, history, and craftsmanship of the automobile at the Hilton Head Island Concours d’Elegance & Motoring Festival, one of the country’s premier automotive lifestyle events. Each fall, collectors and enthusiasts gather on Hilton Head Island to admire rare and historic vehicles while honoring the passion, innovation, and design behind some of the world’s most remarkable automobiles. Beyond showcasing automotive excellence, the nonprofit festival helps support youth organizations and students pursuing careers in the automotive industry.
November
Hilton Head Half & Quarter Marathon & 5K
November 1, 2026
Race Start: 8:00am at Harbour Town at The Sea Pines Resort
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Runners of all levels are invited to experience the beauty of Hilton Head Island during the Hilton Head Half & Quarter Marathon and 5K. Starting at Harbour Town, this scenic race offers participants the chance to explore the island’s beautiful landscapes while competing in a half marathon, quarter marathon, or 5K. Can’t make it to the island? A virtual race option allows runners to participate from anywhere! This event also supports local conservation efforts, benefiting the Sea Pines Forest Preserve Foundation and the Turtle Trackers of Hilton Head.
Hilton Head Oyster Festival
All You Can Eat Event: November 6, 2026
5:00-8:00pm at Shelter Cove Community Park
Festival Day: November 7, 2026
11:00am-5:00pm at Lowcountry Celebration Park
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The Hilton Head Oyster Festival brings two days a year locals and visitors alike always look forward to. The All You Can Eat Event will be held on November 6th, from 5:00-8:00pm at the Shelter Cove Community Park. Here, you’ll be offered all-you-can-eat Lowcountry boil, seafood chowder, pulled pork, and of course, steamed local oysters. This is a rain-or-shine event. The actual festival day is on that Saturday, November 7th, at Lowcountry Celebration Park from 11:00am-5:00pm. A full day of delicious food, great music, artisan pop-up shops, and kid’s activities, a lineup of local bands will be on the main stage for most of the afternoon.
Hilton Head Island Lantern Parade
November 14, 2026
5:30-7:30pm Starting At Alder Lane Beach Access
Experience one of Hilton Head Island’s most magical fall traditions during the annual Lantern Parade, where creativity and community come together for a glowing procession along the beach. Participants showcase handmade lanterns as they walk beneath the beautiful, evening sky, creating a memorable celebration of art, imagination, and island spirit. Event details for 2026 will be announced soon.
Turkey Trot 5K & Fun Walk
November 26, 2026
8:00am-10:00am starting at the Boathouse parking lot
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What better way to start your Thanksgiving than a Turkey Trot? Register your family and friends now for the 38th Annual Turkey Trot hosted by the Island Recreation Association.
Early bird registration is $35, with price increases to $40 after September 16th, and $50 after November 1st. Register online.
