From wine dinners and oyster roasts to concerts, wagon rides, and sparkling holiday lights, there’s something for everyone to enjoy at Sea Pines this holiday season. Whether you’re a longtime resident or a first-time visitor, these fall and winter events are the perfect way to experience the charm of Hilton Head’s most iconic community.
Fall Highlights in Sea Pines
Harbour Town Fall Fest – September 14
Kick off the season with this family-friendly festival featuring live music, local food vendors, and activities for all ages in the heart of Harbour Town.
Hilton Head Island Shrimp Festival – September 20
Seafood lovers rejoice! Sample signature shrimp dishes, enjoy craft brews, and soak up live entertainment at this beloved Harbour Town event.
Halloween Happenings – October 18–26
Sea Pines goes all out for spooky season with Halloween Wagon Rides through the Forest Preserve and Halloween on the Harbour, a festive afternoon of costumes, trick-or-treating, and family fun.
Oyster Roasts at Coast – Beginning October 11
Every Saturday through February, gather oceanfront for a classic Lowcountry tradition: oysters roasted to perfection, paired with breathtaking beach views
Thanksgiving Traditions
Thanksgiving Wagon Rides – November 24–29
Celebrate the holiday week with daily wagon rides through Heritage Farm.
Pre-Turkey Day Dolphin Dash 5K – November 26
Burn some calories before the big meal with this festive run from the Beach Club.
Thanksgiving Day Scavenger Hunt – November 27
A fun way to get the whole family outside and exploring Sea Pines.
Gregg Russell Thanksgiving Concert & Harbour Town Tree Lighting – November 28
Join one of Hilton Head’s most cherished holiday traditions with a visit from Santa, live music under the Liberty Oak, and the official lighting of the Harbour Town Christmas tree
Holiday Magic in Harbour Town
Harbour Town Lights – November 28–January 1
Stroll under twinkling lights, enjoy seasonal shopping, and bask in the holiday spirit as Harbour Town shines bright all season long.
Sandy Sledding – December 27
Trade snowy hills for sandy slopes as kids and adults alike enjoy a one-of-a-kind sledding experience at the Beach Club.
Paws & Claus Parade – December 29
A festive and furry parade featuring beloved pets dressed for the season in Harbour Town.
Gregg Russell Christmas Concert – December 23
Beloved local musician Gregg Russell returns for a holiday sing-along, complete with a special visit from Santa Claus.
Polar Bear Swim – December 30
Brave the chilly Harbour Town Pool waters for this invigorating annual tradition
Seasonal Food & Wine Experiences
Throughout the season, Sea Pines offers a lineup of unforgettable dining experiences:
- Jayson by Pahlmeyer Wine Dinner – September 12
- Angel’s Envy Bourbon Dinner – October 3
- White Walnut Estate Wine Dinner – October 17
- Patrón Dinner – October 30
- Orin Swift Wine Dinner – November 14
- Italian Wine Dinner – December 12
