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!
- Santa & Shopping Day
- Santa Visits at Shelter Cove Towne Centre
- Gregg Russell Thanksgiving Concert & Christmas Tree Lighting
- Caramel Apple Festival
- Holiday Station Lighting at Fire Station 3
- Santa Mail
- Holiday Pops
- Town of Hilton Head Island's Annual Christmas Tree Lighting
- Jevon Daly's Kid Show & Pictures with Santa
- Winter Wonderland Festival
- The Gullah Village at Holiday Nights & Lights
- Hanukkah Celebration and Menorah Lighting
- 2025 Mercedes-Benz of Hilton Head Jingle Jingle Bridge Run
- Nutcracker 5K
The following list is in order by date.
Santa & Shopping Day
November 28, 2025 from 11am-2:30pm
Shelter Cove Harbour & Marina
1 Shelter Cove 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 28 & 29 from 1:30-3:30pm
December 6 from 5:00-7:00pm (at Winter Wonder Festival)
December 20 from 1:00-3:00am (Pet Visits)
December 24 from 1:00-3:00pm
Shelter Cove Towne Center (Near Francesca’s)
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 6th, Santa will be located in the Community Park. Bring Fido on the 20th for Pet Visits with Santa!
Gregg Russell Thanksgiving Concert & Christmas Tree Lighting
November 28, 2025 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.
Caramel Apple Festival
November 29, 2025 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 $18 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.
Holiday Station Lighting at Fire Station 3
November 29, 2025 from 5:00-7:00pm
Fire Station 3
534 William Hilton Parkway,
Hilton Head Island, SC 29928
One of the best holiday light displays on the island, you won’t want to miss the official Holiday Station Lighting at Fire Station 3. The event starts at 5pm, but the actual lighting of the station will be taking place closer to 6pm. Enjoy cookies, hot chocolate, and arts and crafts before and after the lighting, as well as snapping a photo with Santa himself! This event is free to attend, but donations to the Hilton Head Firefighter’s Association as well as new, unwrapped toys and non-perishable food items for Deep Well will be happily accepted.
Santa Mail
November 29-December 18, 2025
All Hilton Head Island Fire Stations
Need to mail your Christmas list to Santa? We have a list of special mailboxes around town at every fire station that will get your letter directly to the North Pole ASAP! Mail your letter by the 18th and you’ll get a response–so don’t forget to put your return address on the envelope! He sure would hate to not have time to write back after that date, but Santa’s a busy guy this time of year!
Station 1: 70 Cordillo Parkway
Station 2: 65 Lighthouse Road
Station 3: 534 William Hilton Parkway
Station 4: 400 Squire Pope Road
Station 5: 20 Whooping Crane Way
Station 6: 12 Dalmatian Lane
Station 7: 1001 Marshland Road
Headquarters: 40 Summit Drive
Holiday Pops
November 30, 2025 at 4:00pm
December 1, 2025 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 Thanksgiving Weekend. Led by Maestro John Morris Russell (JMR), the Hilton Head Symphony Orchestra will perform a range of holiday music from classic favorites and carols, to jazz, R&B, and gospel. This year the HHSO Chorus will be joined by singers from May River High School, and performances by Michael Preacely and Brooklyn Thatcher will wow the crowd. We even hear that the Grinch will be stopping by!
Town of Hilton Head Island’s Annual Christmas Tree Lighting
December 5, 2025 from 5:30-7:30pm
Lowcountry Celebration Park
94 Pope Ave,
Hilton Head Island, SC 29928
The actual tree lighting will be at 6:30pm, but make sure to arrive early for food trucks, cocoa, and a laser light show set to music from local bands. Don’t miss Santa, who’s set to arrive at 5:45pm, and will be glad to meet you until 7pm. Admission is free, and additional parking will be at the USCB campus with The Breeze trolley service running from 5:15-7:30pm. Festive attire is strongly encouraged!
Jevon Daly’s Kid Show & Pictures with Santa
December 6, 13, 20, 21-23, 2025
Show: 11:30am-1:00pm
Pictures with Santa: 1:00-2:30pm
Coligny Center Stage
1 N Forest Beach Dr,
Hilton Head Island, SC 29928
Every Saturday in December (plus additional dates), head to Coligny Plaza for kid-friendly live entertainment with a chance to meet Santa to follow! Jevon Daly will be at Coligny’s Center Stage to perform a holiday version of his Kid Show, a kid-centric storytelling adventure. He’ll be on stage from 11:30am-1:00pm, but make sure to stick around to take pictures with Santa starting at 1pm.
If you haven’t send your letter to Santa, Coligny will have Santa’s Post Office that’ll send it direct to the North Pole. Plus, if you shop or dine anywhere in Coligny throughout the month of December, you can enter to win $1000!
Winter Wonderland Festival
December 6, 2025 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. Santa has RSVP’d to this event, so make sure to bring your camera!
The Gullah Village at Holiday Nights & Lights
December 6-8, 2025 from 6:00-8:00pm
Historic Mitchelville Freedom Park
40 Harriet Tubman Way,
Hilton Head Island, SC 29926
See this dazzling light and holiday display at the Historic Mitchelville Freedom Park. In its sixth year, the park will once again be transformed, welcoming cars filled with cheery visitors looking for some holiday magic and Christmas lights. Grab some hot cocoa to-go, turn on a radio station with some Christmas music, and join in on the fun!
Admission is free, but donations are accepted. This is a popular event, so if you’d like to avoid long waits, plan to line up on Beach City Road at about 5:45pm.
Hanukkah Celebration and Menorah Lighting
December 14, 2025 from 5:30-6:30pm
Lowcountry Celebration Park
94 Pope Ave,
Hilton Head Island, SC 29928
Celebrate the Jewish holiday, Hanukkah, with the Hilton Head Island community at this free event. Rabbi Brad L. Bloom of Congregation Beth Yam will lead the Menorah lighting ceremony, and attendees will be able to enjoy traditional holiday food like latkes and sufganiyot, as well as music, dreidel games and more.
2025 Mercedes-Benz of Hilton Head Jingle Jingle Bridge Run
December 21, 2025 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.
Nutcracker 5K
TBD
Stay tuned for more information about this event!
