Did you finally book that Hilton Head getaway for October 2025? Props! You chose the best month to visit the island.
October is still fall season, meaning you’ll get that hint of chill in the air but with the warmth that Hilton Head is known for year-round. The most exciting part? The month is packed with occasions.
Here are ten events we think you absolutely shouldn’t miss.
The Lowcountry Fish & Grits Music Festival
Address: 94 Pope Avenue, Hilton Head Island, SC 29928
Phone: N/A
The Lowcountry Fish & Grits Music Festival is a big love letter to the Gullah Geechee culture, a community with deep roots here and connections stretching all the way to the African diaspora. It’s a day of incredible live music, vibrant performances, and local cuisine that’ll make you say, “Okay, I’m not eating anywhere else for the rest of my trip.”
That’ll be on October 4th, 2025, from 12:00 PM to 6:00 PM at Lowcountry Celebration Park!
Fall Native Plant Sale
Address: 70 Honey Horn Drive, Hilton Head Island, SC 29926
Phone: (843) 689-6767
Oconee Azalea, Beautyberry, and Wild Black Cherry? Nope, it’s not the lineup for a new indie band but some of the gorgeous native plants you can pick up at the Fall Native Plant Sale at the Coastal Discovery Museum!
If you love gardening or just want to bring a little piece of Hilton Head’s natural beauty home, swing by on October 4th, 2025, from 10:00 AM to 1:00 PM.
Hounds on the Harbour
Address: 149 Lighthouse Road, Hilton Head Island, SC 29928
Phone: (843) 842-1979
Calling all dog lovers! Hounds on the Harbour is a doggie dream day in Harbour Town. Bring your pup (or meet a bunch of adorable ones) and enjoy raffles, a live DJ, and dog-friendly activities, including the famous pupcake walk.
Hilton Head Humane will be there with canines ready for adoption. This event is also on October 4th, 2025, from 10:00 AM to 12:00 PM.
Jeep Island
Address: 138 Island Drive, Hilton Head Island, SC 29926 / 94 Pope Avenue, Hilton Head Island, SC 29928 / 59 Pope Ave, Hilton Head Island, SC 29928
Phone: N/A
On October 10th and 11th, 2025, Jeep Island will welcome fans of Jeeps, chili, and music. Keep your eyes peeled for the star of this annual festival: the raffle for a 2002 Jeep Wrangler TJ! You don’t even have to be there to win…
Jeep Island supports the Island Recreation Center’s Children Scholarship Fund. Go to Lincoln and South Brewing Company for the meet-and-greet, Lowcountry Celebration Park for the main event, and The Bank for the after-party.
Pumpkin Patch
Address: 39 Shelter Cove Lane, Hilton Head Island, SC, 29928
Phone: (843) 681-7273
Nothing says fall like pumpkins and costumes. So, join the Pumpkin Patch by the Island Recreation Center this October 17th! Let the kids don their Halloween fits and compete to win the contest. There’ll be bounce houses, games, and free pumpkins from 4:00 PM to 7:00 PM.
Parents, events at the Shelter Cove Park are the perfect way to make your young ones burn off some energy. Be ready!
Italian Heritage Festival
Address: 70 Honey Horn Drive, Hilton Head Island, SC 29926
Phone: N/A
Are you craving pasta, pastries, and maybe a little grape stomping (yes, really)? The Italian Heritage Festival on October 18th, 2025, at the Coastal Discovery Museum is for you. It’s all things Italian, with booths serving everything from meatballs and calzones to gelato and zeppolis from 11:00 AM to 4:00 PM.
There’ll be a silent auction with prizes like golf outings, boat cruises, spa days, and gift baskets, too. Thanks, Italian American Club of Hilton Head Island!
Gullah Food Festival
Address: 12 Georgianna Drive, Hilton Head Island, SC 29926
Phone: N/A
The Gullah Food Festival is a feast of history and tradition. Hosted by the Gullah Museum of Hilton Head Island, the event serves up authentic dishes that have been passed down for generations.
Taste the culture, meet locals who’ve lived it, and maybe even hear a few stories while you’re in line for seconds. Write the details down: October 18th, 2025, from 11:00 AM to 4:00 PM.
Dvořák Cello Concerto
Address: 540 William Hilton Parkway, Hilton Head Island, SC 29928
Phone: (843) 842-2055
For a change of pace, settle into the elegant sounds of the Hilton Head Symphony Orchestra at First Presbyterian Church. Conducted by John Morris Russell, with Christine Lamprea on cello, the Dvořák Cello Concerto promises two evenings of pure musical magic.
Even if you’re not a classical music buff, you’ll appreciate hearing world-class musicians perform in an intimate, beautiful setting. Buy your tickets for October 19th or 20th, 2025!
Halloween on the Harbour
Address: 149 Lighthouse Road, Hilton Head Island, SC 29928
Phone: (843) 842-1979
What about some spooky seaside fun from 1:30 PM to 3:30 PM? Halloween on the Harbour will be holding games, trick-or-treats, and a Halloween fashion show under the famous Liberty Oak!
Whether you’re five or fifty-five, costumes are encouraged. Bring your witch hats, pirate boots, or superhero capes on October 26th, 2025.
Concours d’Elegance & Motoring Festival
Address: 1 Cardinal Court, Hilton Head Island, SC 29926
Phone: (843) 785-7469
Closing out October with style, the Hilton Head Island Concours d’Elegance & Motoring Festival is where art meets automotive excellence. Stroll through a showcase of classic cars, luxury vehicles, and cutting-edge designs!
It’s as much about beauty as it is about horsepower, and the whole thing feels like stepping into a moving art gallery. Events roll out from October 29th to November 2nd, 2025.
Have a Buzzing October on the Island!
Wow. That’s a busy October 2025! We’re talking delicious foods, educational gatherings, cultural celebrations, music that moves you, spooky fun, and jaw-dropping cars. We hope you’ll have enough time to explore…
At Beachside Hilton Head’s vacation rentals, we’ll make sure your mornings start energized (with coffee, sunshine, and views) and your nights restful. You’ll leave with a camera full of memories, a heart full of joy, and (let’s be honest) maybe a few extra pounds. But hey, that’s the sign of a vacay well spent.
There are countless events to witness. Book your stay at Beachside Hilton Head now!
