The island’s holiday schedule is packed with performances, tree lightings, festivals, markets, and more! We’ve collected some of the most anticipated events happening on Hilton Head leading up to the end of the year. We’ll keep an eye out for more events and update this list throughout the month.
On the hunt for the best Christmas lights on the island? Read our guide now!
- Town's Official Holiday Kick-Off Festival
- Hilton Head Island Lantern Parade
- Santa & Shopping Day
- Santa Visits at Shelter Cove Towne Centre
- Caramel Apple Festival
- Gregg Russell Thanksgiving Concert & Christmas Tree Lighting
- Hilton Head Symphony Orchestra's Holiday Pops
- Winter Wonderland Festival
- Town of Hilton Head Island's Annual Christmas Tree Lighting
- Holiday Nights & Lights at Historic Mitchelville Freedom Park
- Polar Pines Express Holiday Wagon Ride
- Gregg Russell Christmas Concert
- 2025 Mercedes-Benz of Hilton Head Jingle Jingle Bridge Run
- Paws and Claus Parade
- Holiday Fun in Harbour Town
- Nutcracker 5K
The following list is in order by date.
Town’s Official Holiday Kick-Off Festival
November 14, 2026 from 11:30am-2:30pm
Arts Center of Coastal Carolina
14 Shelter Cove Ln,
Hilton Head Island, SC 29928
Usher in the holiday season with this free, fun community festival filled with holiday entertainment from local groups, arts and crafts for all ages, delicious treats from food trucks, and a wonderful Art Market featuring the creations of local artisans. We’ve even heard that Santa and Mrs. Claus is set to arrive in style on an antique fire truck and will be able to visit with children. There will also be a performance from the cast members of the Arts Center’s Annie!
Hilton Head Island Lantern Parade
November 14th, 2026 at 5:00pm
Alder Lane Beach Access
2 Woodward Ave,
Hilton Head Island, SC 29928
One of the most magical events held on Hilton Head, the annual Lantern Parade is an amazing chance for guests and residents to celebrate the island’s history and community. This free event lights up the night sky at Coligny Beach, and showcases the creations of artist, Chantelle Rytter, alongside other custom-made lanterns. This year, the Black Sheep Ensemble, Soda City Band, United States Marine Corps Dirty Boots Brass Band, and the Atlanta Drum Academy will join in on the fun.
Need to make a lantern? Check our calendar for various lantern making workshops in the weeks before the parade!
Santa & Shopping Day
November 27, 2026 from 11am-2:30pm
Shelter Cove Harbour & Marina
1 Harbourside Ln,
Hilton Head Island, SC 29928
All are welcome to join in on the holiday fun at Shelter Cove Harbour & Marina. Starting at 11am, sing along to holiday music, jump on a bounce house, and enjoy a train ride (additional cost) around the marina! The first 300 kids will be given a gingerbread cookie kit provided by the Hilton Head Social Bakery and sponsored by the Shelter Cove Merchants. Holiday sales and dining specials at participating stores and restaurants will be happening all day.
At noon, Santa will arrive aboard a fire truck, and he’ll be available for pictures at Neptune’s statue until 2:30pm.
This is a free event, however we’d like to spread the holiday cheer, so bring an unwrapped toy or canned items for the Deep Well Project. Learn more about this local non-profit.
Santa Visits at Shelter Cove Towne Centre
November 27 & 28 from 1:30-3:30pm
December 19 from 1:00-3:00am (Pet Visits with Santa)
December 24 from 1:00-3:00pm
Shelter Cove Towne Center
40 Shelter Cove Ln,
Hilton Head Island, SC 29928
Santa will be making various visits to Shelter Cove Towne Centre this holiday season, making it easy for your kiddos to see the jolly fellow. You’ll find him close to the store, Francesca’s, but on the December 24th, Santa will be located at the tree in the park. Bring Fido on the 19th for Pet Visits with Santa to benefit Hilton Head Humane!
Caramel Apple Festival
November 27, 2026 from 1:00-3:00pm
Heritage Farms
Greenwood Dr,
Hilton Head Island, SC 29928
Head to Sea Pines Heritage Farm, where your family will have a fun-filled afternoon full of games, delicious caramel apples, and a bounce house to take care of that sugar rush! Choose to purchase a $20 all-inclusive ticket, or it’ll be $6 per apple. And remember, there is a fee to enter the Sea Pines property at either of the two gates.
Gregg Russell Thanksgiving Concert & Christmas Tree Lighting
November 27, 2026 from 7:30-9:00pm
Liberty Oak in Harbour Town
147 Lighthouse Rd,
Hilton Head Island, SC 29928
You’ll typically find the island icon, Gregg Russell, performing under the Liberty Oak in Harbour Town during the warm summer nights, but don’t miss his special Thanksgiving concert that’s family-friendly and completely festive! Get into the holiday spirit by sticking around to see the official lighting of the Harbour Town Christmas Tree! Rumor has it that Santa Claus might stop by from 5:30-7pm. Passes are available to purchase at both Sea Pines gates to enter the property, but this event is completely free to attend.
Hilton Head Symphony Orchestra’s Holiday Pops
November 29, 2026 at 4:00pm
November 30, 2026 at 7:30pm
First Presbyterian Church
540 William Hilton Pkwy,
Hilton Head Island, SC 29928
A favorite family tradition on the island, Holiday Pops returns this holiday season. Led by Maestro John Morris Russell (JMR), the Hilton Head Symphony Orchestra will perform a range of holiday music that brings generations together. This year the HHSO Chorus will be joined by American Idol and Broadway star, Melinda Doolittle, as well as the Youth Concerto Competition winner, Mana Takahashi.
Winter Wonderland Festival
December 4, 2026 from 4:00-7:00pm
Shelter Cove Community Park
39 Shelter Cove Lane,
Hilton Head Island, SC 29928
For a major dose of holiday family fun, head to the Annual Winter Wonderland Festival at Shelter Cove. This event doesn’t require tickets, and includes free bounce houses, DJ and more family fun! Food and drinks, along with a few other family-friendly activities will be an additional cost. There will also be a Golden Candy Cane Hunt at 5:30pm.
Town of Hilton Head Island’s Annual Christmas Tree Lighting
December 5, 2026 from 5:30-7:30pm
Lowcountry Celebration Park
94 Pope Ave,
Hilton Head Island, SC 29928
Stay Tuned for More Information
Holiday Nights & Lights at Historic Mitchelville Freedom Park
December 5-7, 2026
Historic Mitchelville Freedom Park
40 Harriet Tubman Way,
Hilton Head Island, SC 29926
Stay Tuned for More Information
Polar Pines Express Holiday Wagon Ride
December 19, 2026 at 1:00pm
Heritage Farm
185 Greenwood Dr,
Hilton Head Island, SC 29928
What’s more fun than a festive wagon ride traveling to Sea Pines’ version of the North Pole? Enjoy crafts and other activities along with hot chocolate and treats while singing carols and listening to the famous story, “The Polar Express.” Seats will sell out on this ride, so make sure you make your reservations!
Gregg Russell Christmas Concert
December 23, 2026 from 7:30-9:00pm
Liberty Oak Tree in Harbour Town
147 Lighthouse Rd,
Hilton Head Island, SC 29928
The famous Gregg Russell will take the Liberty Oak stage once again this holiday season, playing his guitar and singing holiday songs during this island-favorite tradition. Everyone is welcome to celebrate the season at this free event–even Santa will be there from 5:30-7pm and then again after the show.
2025 Mercedes-Benz of Hilton Head Jingle Jingle Bridge Run
December 24, 2026 at 8:00am
Crossings Park
4 Haig Point Ct,
Hilton Head Island, SC 29928
Join in on Hilton Head’s holiday tradition since 1992, and participate in either the 5K run or the 10K Road Race hosted by Bear Foot Sports. While the courses start and finish at Crossings Park, everyone will run over Broad Creek on the Cross Island Expressway. While you’ll also receive a long-sleeved custom t-shirt along with jingle bells, participants are encouraged to get in the spirit of the season by wearing elf, Santa, or other holiday-inspired costumes. Stick around for the award ceremony for refreshments, music, and door prizes after the race. Who knows, Santa might even stop by! Register online and find more information on the race’s website.
Paws and Claus Parade
December 27, 2026 from 1:00-2:00pm
Harbour Town
149 Lighthouse Rd,
Hilton Head Island, SC 29928
Keep the fun going after Christmas during this year’s Paws and Claus Parade, where your furry friends can show off their holiday attire in a parade led by Jolly Saint Nick. A great photo opportunity (is it too early to think about next year’s Christmas cards?) and a great way to see adorable dogs! Registration begins at 12:30pm in front of the Quarterdeck Market. Stick around after the parade to enjoy dog games around the Liberty Oak stage.
Holiday Fun in Harbour Town
December 27 & 28, 2026 from 5:00-7:30pm
Harbour Town
149 Lighthouse Rd,
Hilton Head Island, SC 29928
The holiday magic is not over yet! Join in on the fun around the Liberty Oak Tree in Harbour Town to watch classic holiday movies, roast marshmallows, and enjoy train rides around the harbour with family and friends. Both the movie and marshmallow roasting is scheduled to start at 6pm–both of which are complimentary with a donation of a canned food item for Deep Well. Train rides are $6 per passenger and tickets can be purchased ahead of time online.
Nutcracker 5K
TBD
Hilton Head Running Company’s Website
Stay tuned for more information about this event!
