Hilton Head Christmas Events You Don't Want to Miss
Updated for 2026
By Jennifer Jeffcoat
Jennifer writes for Beachside Getaway, sharing travel tips, top things to do, and the best places to stay to help guests make the most of their Hilton Head Island vacation.
Looking for the best Hilton Head Christmas events this year? Hilton Head Island celebrates the season in its own coastal way. Families gather under the Liberty Oak in Harbour Town for free concerts with Gregg Russell. Kids hop on holiday train rides around the harbor, decorated dogs parade behind Santa, and you can even build a sled and race it on the beach. Visiting Hilton Head in December means mild weather, waterfront views, and plenty of small-town holiday spirit. Whether you're planning a full week or a quick getaway between family gatherings, here are the events that make Christmas in Hilton Head Island so special.
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In This Article
- Live Music & Holiday Performances
- Outdoor Holiday Fun
- Parades & Festive Gatherings
- Holiday Lights & Santa Visits
- Book Your Holiday Rental
- FAQs
Live Music & Holiday Performances
Gregg Russell's Christmas Concert Under the Liberty Oak
No Hilton Head Christmas is complete without Gregg Russell. The beloved performer has entertained families under the Liberty Oak in Harbour Town for decades. His Christmas show is full of carols, sing-alongs, and the playful audience participation he's known for.
Santa arrives before the concert and stays afterward, so plan to come early for photos. Bring blankets or lawn chairs to claim a good spot on the lawn. Sea Pines charges a $10 daily gate fee per vehicle, for anyone not staying within the resort.
- Date: Wednesday, December 23, 2026
- Time: 7:30–9 PM (Santa visits 5:30–7 PM and after the show)
- Location: Liberty Oak, Harbour Town, 147 Lighthouse Rd., Sea Pines
- Cost: Free
See Beachside Getaway Sea Pines Vacation Rentals
Hilton Head Choral Society: "A Holiday Tapestry"
The Hilton Head Choral Society brings its talented singers together for a holiday concert full of beloved carols and seasonal favorites. It's one of the island's most cherished holiday traditions, and it often sells out. Buy your tickets early through the Choral Society's website or by calling (843) 341-3818.
- Date: Friday, December 11, 2026
- Time: 7 PM
- Location: First Presbyterian Church, 540 William Hilton Pkwy.
- Cost: $15–$40
Cheyenne Jackson: "Suspiciously Merry"
Broadway and TV star Cheyenne Jackson brings his holiday show to the Arts Center of Coastal Carolina. Expect seasonal classics delivered with his big voice and charm. There are two performances, and one is a matinee, making it easy to attend even if you have younger travelers or evening plans.
- Date: Tuesday, December 15, 2026
- Time: 4 PM and 7:30 PM
- Location: Arts Center of Coastal Carolina, 14 Shelter Cove Ln.
- Cost: Tickets from $63
Annie at the Arts Center of Coastal Carolina
This year's holiday musical at the Arts Center is Annie, a feel-good classic about hope that fits the season perfectly. Take the kids to hear classics like “Tomorrow” and “It’s a Hard Knock Life” and enjoy this memory-making holiday activity perfect for all ages. The show runs through the new year, so there are plenty of chances to see it.
- Dates: December 2, 2026–January 3, 2027
- Time: Showtimes vary by performance
- Location: Arts Center of Coastal Carolina, 14 Shelter Cove Ln.
- Cost: $66 adults / $61 children (regular pricing)
Outdoor Holiday Fun
Polar Pines Express
Climb aboard a festive wagon ride through Sea Pines' wooded trails. Holiday stories, cheerful music, hot chocolate, and plenty of Christmas spirit come along for the ride on this cozy outing the whole family will love. Spots fill quickly on this one-day activity, so call (843) 842-1979 to reserve.
- Date: Saturday, December 19, 2026
- Time: 1 PM
- Location: Heritage Farm, 185 Greenwood Dr., Sea Pines
- Cost: Kids ages 3-12 are $22 | Adults ages 13+ are $24
Sandy Sledding
You won't find snow on Hilton Head Island, but you will find sand sledding! Sea Pines puts a coastal twist on a winter tradition and lets little ones slide down the dunes in a friendly competition to see whose homemade sled is the best! Reservations are required.
- Date: Monday, December 28, 2026
- Time: 1–2:15 PM
- Location: Sea Pines Beach Club, 87 N. Sea Pines Dr.
- Cost: $60 per team of up to 6 people
Holiday Lights Wagon Ride
Take an illuminated wagon ride through the forest preserve as you view beautiful holiday lights throughout Sea Pines after dark. There will be holiday carols, warm beverages, and lots of holiday spirit!
- Date: Tuesday, December 29, 2026
- Time: 5–6 PM
- Location: Heritage Farm, 185 Greenwood Dr., Sea Pines
- Cost: Kids ages 3-12 are $25 | Adults ages 13+ are $30
Audubon Christmas Bird Count
Nature lovers can join one of the longest-running citizen science projects in the country. Volunteers spend the day counting birds at sites across the island. The results help scientists track bird populations, and no experience is needed. Learn more about this wonderful voluntourism opportunity here: The Audubon Christmas Bird Count.
- Date: Monday, December 14, 2026
- Time: All day; times vary by group
- Location: Various sites across Hilton Head Island
- Cost: Free
Parades & Festive Gatherings
Paws and Claus Parade
Pups in their holiday best parade through Harbour Town in this cheerful, tail-wagging event. Bring your own festively dressed dog to join in, or just come to watch.
- Date: Sunday, December 27, 2026
- Time: 1–2 PM
- Location: Quarterdeck Market to the Liberty Oak stage, Harbour Town
- Cost: Free
Holiday Fun in Harbour Town
Spend two evenings soaking up the season in Harbour Town. There will be train rides every 5 to 10 minutes starting at 5 PM, holiday movies, marshmallow roasting, and more! Bring a canned good to donate.
- Dates: December 27–28, 2026
- Time: 5–7:30 PM
- Location: Harbour Town, Sea Pines
- Cost: Free with a canned food donation; train rides cost $6.
Town of Hilton Head Island Tree Lighting
Watch the town's official Christmas tree light up at Lowcountry Celebration Park, with festive entertainment for the whole family. It's an easy way to kick off the holidays near the beach.
- Date: Saturday, December 5, 2026
- Time: [Confirm time]
- Location: Lowcountry Celebration Park, 94 Pope Ave.
- Cost: Free
Coastal Christmas Market
Shop local makers and vendors for unique gifts at this oceanfront holiday market. It's a great place to find a one-of-a-kind souvenir from your trip.
- Dates & Times: Saturday, December 5, 4–9 PM; Sunday, December 6, 10 AM–5 PM
- Location: Beach House Resort, 1 S. Forest Beach Dr.
- Cost: Free admission
Winter Wonderland Festival
This favorite island festival brings carnival games, hayrides, and holiday fun for families. Read our complete Winter Wonderland guide to plan your visit.
- Date: Friday, December 4, 2026
- Time: 4–7 PM
- Location: Shelter Cove Community Park
- Cost: Free
Holiday Lights & Santa Visits
Twinkling lights and visits with Santa are part of what makes Christmas in Hilton Head Island so special. Displays like Harbour Town Lights, Shelter Cove's holiday lights, and the Dove Street Festival of Lights brighten the island all season. Check out our guide to Christmas on Hilton Head for where to see the best displays and meet Santa.
Book Your Holiday Rental Directly With Beachside Getaway
Featured Property: 7 Dove Street
Make this the year your family spends Christmas on Hilton Head Island. When you book directly with Beachside Getaway, you can choose from a wide selection of vacation rentals with plenty of room for the whole family. Our local team is happy to help you find the perfect home for your holiday stay. Contact us today to plan your holiday getaway.
See All Hilton Head Vacation Rentals
Frequently Asked Questions
Are Hilton Head Christmas events free?
Many are! The Gregg Russell Christmas concert, Paws and Claus Parade, tree lighting and Coastal Christmas Market are free to attend. Concerts at the Arts Center and the Choral Society performance need tickets.
Do I need reservations for holiday events?
Some events need them. Sandy Sledding requires a reservation, and the Polar Pines Express fills quickly. Book ticketed shows early, especially the Choral Society concert.
What is Hilton Head like in December?
Hilton Head in December is mild and peaceful. Daytime temperatures are comfortable for walks, bike rides and outdoor events, and evenings are cool enough for a cozy sweater.
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