It’s a cool 59 degrees on Hilton Head Island this morning. The sun is shining, and fall is officially here. As the mild temps make themselves comfortable (and us), now is the perfect time to plan your next Island getaway!
This time of year, the town’s calendar is packed, meaning there’s always something fun happening no matter what you may be interested in. From food festivals to car shows and turkey trots to Santa meet-and-greets, you can fill your vacation with exciting holiday events on Hilton Head. This month, we’ve got the scoop on everything happening from Halloween to Christmas. So be sure to check out these top 10 events and add some local festivities to your next visit.
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1. Pumpkin Patch
October 18 | 4 – 7 PM | Shelter Cove Community Park
Kickoff the fall festivities with the Pumpkin Patch at Shelter Cove Community Park. This family-friendly event features bounce houses, games, a Halloween costume contest at 5:45 PM, and other fun activities for kids of all ages. Enjoy concessions, train rides, and a rock-climbing wall to make the day even more exciting.
2. Halloween Wagon Ride
10/19 and 10/26 | Starts at 11:30 AM | Heritage Farms on Greenwood Drive
Enjoy a spooky and fun-filled wagon ride through the Sea Pines Forest Preserve. The ride includes Halloween-themed games, and kids are encouraged to come in costume. It’s a perfect way to celebrate Halloween with the little ones without the frights that come at night. Reservations are required, so be sure to secure your spot early.
3. Italian Heritage Fest
October 19 | 11 AM – 4 PM | The Coastal Discovery Museum at Honey Horn
Celebrate Italian culture at the Hilton Head Italian Heritage Fest, where you can enjoy authentic Italian food, lively music, and beloved traditions. The event also features a bocce tournament, grape stomping, and even a pizza-eating contest! This annual festival is a wonderful way to immerse yourself in Italian heritage while supporting local charities. Be sure to come hungry!
4. Halloween on the Harbour
October 27 | 1:30 – 3:30 PM | Harbour Town – 149 Lighthouse Road
Join the fun at Harbour Town, where kids can trick-or-treat and participate in a Halloween costume parade on the Liberty Oak stage. This spooktacular event offers a festive atmosphere with activities and games for all ages. Costumes are encouraged, and there will be plenty of treats to go around.
5. Hilton Head Island Concours d’Elegance & Motoring Festival
October 31 – November 3 | Various Locations
This premier automotive event on Hilton Head Island showcases stunning vintage cars, luxury vehicles, and classic motorcycles. The festival includes a wide range of activities like the Car Club Showcase, Aero Expo, a film fest, and driving tours and culminates in the Concours d’Elegance, where the finest vehicles compete for top honors. With more roughly 200 cars and 75 judges from across all of North America, it’s a can’t-miss weekend for car enthusiasts.
6. Hilton Head Oyster Festival
November 8-9 | 11 AM – 5 PM on the 9th | Shelter Cove Community Park & Lowcountry Celebration Park
The Hilton Head Oyster Festival is a two-day, all-you-can-eat celebration of local seafood, particularly the island’s famous oysters. In addition to oysters prepared in a variety of ways, the festival features live music, a kid’s zone, and plenty of other dining options. It’s a perfect way to savor the flavors of the Lowcountry while enjoying the fall weather. Enjoy live entertainment, pop-up shops, and artisan goods. And don’t be late for the 2 PM oyster shucking contest!
7. Town’s Official Holiday Season Kick-Off Festival
November 16 | 12 – 3 PM | Arts Center of Coastal Carolina
Get into the Christmas spirit with the town's official holiday season kick-off at the Arts Center of Coastal Carolina. This immersive event includes live music, children’s activities, and visits with the Big Man, himself, as Santa and Mrs. Claus arrive in style riding an antique fire truck! The event also serves as the perfect opportunity to begin your holiday shopping with local artisans and vendors showcasing unique, one-of-a-kind creations. Find everything from stocking stuffers to beautiful gifts when you visit.
8. Hilton Head Island Lantern Parade
November 23 | 5:45 – 9 PM | South Forest Beach
The Lantern Parade is a magical celebration where participants and spectators alike light up the night with handmade lanterns. The parade starts at South Forest Beach and follows a scenic route along the shoreline, creating a stunning visual display. Spectators are encouraged to join in the fun by crafting their own lanterns to carry in the procession.
9. Turkey Trot 5K Fun-Run
November 28 | 8 – 10:40 AM | 397 Squire Pope Rd.
This Thanksgiving tradition invites runners and walkers of all ages to participate in a 5K fun-run through scenic Hilton Head. The race starts and ends at 397 Squire Pope Rd, with proceeds benefiting local charities. After the run, participants can enjoy refreshments and festivities with fellow runners. It’s the perfect way to jumpstart Thanksgiving Day!
10. Santa At Shelter Cove
November 29 | 12 – 2:30 PM | Shelter Cove Harbour & Marina
Bring the kids to a winter wonderland to meet Santa at Shelter Cove, where they can share their Christmas wish lists and pose for adorable photos. This festive event is one of the most popular holiday events on Hilton Head and is filled with seasonal cheer, offering families the perfect way to kick off the Christmas season. In addition to Santa visits, there will be holiday-themed activities for kids, bounce houses, train rides, and carols flooding the air. The first 250 kids also get a free gingerbread cookie to take home provided by Hilton Head Social Bakery. Come early, Santa will have to head to the North Pole at 2:30 PM.
Book Your Holiday Getaway to Hilton Head Island
Featured Property: 6 East Wind
With a full calendar of holiday events on Hilton Head, the only thing standing between you and these festive feats is booking your vacation rentals! At Island Getaway Rentals, we have you covered! Book directly with us and save vital holiday money by avoiding the third-party fees Airbnb and VRBO love to add to your bottom line. Plus, with us, you get the additional bonus of working with on-island locals who live in and know this area inside and out.
From restaurant recommendations to help finding your dream rental, we’re available to help every step of the way. Browse our complete list of Hilton Head vacation rentals and book your stay directly with us today!