Holiday Events on Hilton Head Island: Your 2025 Guide
Hilton Head Island is full of festive spirit each winter, offering everything from concerts and parades to tree lightings, markets, and family-friendly celebrations. If you’re planning a holiday getaway—or you’re a local looking for some seasonal fun—here’s a roundup of this year’s most anticipated events happening from Thanksgiving through the end of December.
(And if dazzling light displays are on your holiday bucket list, don’t miss our full guide to the island’s best Christmas lights!)
Events below are listed in date order.
Santa & Shopping Day
📅 November 28, 2025
⏰ 11am–2:30pm
📍 Shelter Cove Harbour & Marina, 1 Shelter Cove Ln
Kick off the holiday weekend at Shelter Cove Harbour & Marina, where families can enjoy live holiday music, bounce houses, and a festive train ride around the marina (additional fee applies). The first 300 kids will receive complimentary gingerbread cookie kits courtesy of Hilton Head Social Bakery and the Shelter Cove Merchants.
Local shops and restaurants will be running seasonal sales and specials all day long.
At 12pm, Santa makes his grand entrance by fire truck, then sticks around for photos at Neptune’s statue until 2:30pm.
Admission is free, but guests are encouraged to bring canned food or an unwrapped toy to support The Deep Well Project.
Santa Visits at Shelter Cove Towne Centre
📅 November 28 & 29 (1:30–3:30pm)
📅 December 6 (5:00–7:00pm during Winter Wonderland Festival)
📅 December 20 (1:00–3:00pm – Pet Photos)
📅 December 24 (1:00–3:00pm)
📍 Shelter Cove Towne Centre, 40 Shelter Cove Ln, near Francesca’s
Santa will be popping up throughout the season at Shelter Cove Towne Centre, giving families plenty of chances for photos and holiday cheer. Most appearances take place near Francesca’s, except for December 6 when he’ll be greeting kids at the Community Park.
Pet lovers—December 20 is your day! Bring your furry family members for special pet-friendly Santa photos.
Gregg Russell Thanksgiving Concert & Christmas Tree Lighting
📅 November 28, 2025
⏰ 7:30–9:00pm
📍 Liberty Oak, Harbour Town, 147 Lighthouse Rd
Beloved island entertainer Gregg Russell returns for his annual Thanksgiving performance under the Liberty Oak—a festive family tradition. The concert leads up to the lighting of the Harbour Town Christmas Tree, a highlight of the evening.
Rumor has it Santa will be greeting families before the show from 5:30–7pm.
Entry to Sea Pines requires a gate pass, but the event itself is free.
Caramel Apple Festival
📅 November 29, 2025
⏰ 1:00–3:00pm
📍 Heritage Farm, Sea Pines
Spend an afternoon at Heritage Farm enjoying carnival-style games, bounce houses, and of course—delicious caramel apples. Choose from a $18 all-inclusive ticket or $6 per apple.
Remember: entry into Sea Pines requires a gate fee.
Holiday Station Lighting at Fire Station 3
📅 November 29, 2025
⏰ 5:00–7:00pm (lighting at approximately 6:00pm)
📍 Fire Station 3, 534 William Hilton Parkway
Fire Station 3 hosts one of Hilton Head’s most impressive seasonal light displays. Arrive early to enjoy cookies, hot chocolate, and holiday crafts before the official lighting. Santa will also be stopping by for photos!
Admission is free, but donations to the Hilton Head Firefighters Association, along with toys and non-perishable food items for Deep Well, are gratefully accepted.
Santa Mail
📅 November 29–December 18, 2025
📍 All Hilton Head Island Fire Stations
Kids can drop off letters to Santa at special North Pole mailboxes located at every fire station. Be sure to mail them by December 18 to receive a personalized response—don’t forget to include a return address!
Mailbox Locations:
- 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 at 4:00pm
📅 December 1 at 7:30pm
📍 First Presbyterian Church, 540 William Hilton Pkwy
Holiday Pops—a beloved tradition—returns with a festive program led by Maestro John Morris Russell. The Hilton Head Symphony Orchestra, along with the HHSO Chorus and guest performers, will bring classic carols, gospel, jazz, R&B, and more to life.
This year’s show features singers from May River High School, plus appearances from Michael Preacely and Brooklyn Thatcher. Keep an eye out…the Grinch might even make a surprise visit.
Town of Hilton Head Island Annual Christmas Tree Lighting
📅 December 5, 2025
⏰ 5:30–7:30pm (tree lighting at 6:30pm)
📍 Lowcountry Celebration Park, 94 Pope Ave
Celebrate the season with live music, food trucks, hot cocoa, and a lively laser light show. Santa will arrive at 5:45pm and meet with families until 7pm.
Parking is available at the USCB campus, with Breeze trolley service running throughout the event. Admission is free; festive attire encouraged!
Jevon Daly’s Kid Show & Photos with Santa
📅 December 6, 13, 20, 21–23, 2025
⏰ Jevon Daly’s Kid Show: 11:30am–1:00pm
⏰ Santa Photos: 1:00–2:30pm
📍 Coligny Center Stage, 1 N Forest Beach Dr
Spend your Saturday at Coligny Plaza with Jevon Daly’s lively holiday version of his Kid Show—packed with storytelling, music, and family fun. Afterward, Santa will be available for photos at Coligny’s Center Stage.
Don’t miss Santa’s Post Office, where kids can send letters straight to the North Pole. Shoppers and diners at Coligny can also enter a $1,000 giveaway throughout December.
Winter Wonderland Festival
📅 December 6, 2025
⏰ 4:00–7:00pm
📍 Shelter Cove Community Park, 39 Shelter Cove Lane
The Winter Wonderland Festival returns with free bounce houses, music, and festive family activities. Food, drinks, and select attractions will have separate fees.
The Golden Candy Cane Hunt starts at 5:30pm—kids won’t want to miss it. Santa will also be on hand for photos.
The Gullah Village at Holiday Nights & Lights
📅 December 6–8, 2025
⏰ 6:00–8:00pm
📍 Historic Mitchelville Freedom Park, 40 Harriet Tubman Way
Experience a magical, drive-through holiday lights display set within Historic Mitchelville Freedom Park. Now in its sixth year, this event draws visitors from across the island for a glowing, music-filled celebration.
It’s free to attend, though donations are appreciated. To avoid long lines, plan to arrive along Beach City Road by 5:45pm.
Hanukkah Celebration & Menorah Lighting
📅 December 14, 2025
⏰ 5:30–6:30pm
📍 Lowcountry Celebration Park, 94 Pope Ave
Join the community for Hilton Head’s annual Hanukkah celebration, featuring the Menorah lighting led by Rabbi Brad L. Bloom. Guests will enjoy traditional Hanukkah treats like sufganiyot and latkes, plus music, dreidel games, and more. This event is free and open to all.
2025 Mercedes-Benz of Hilton Head Jingle Jingle Bridge Run
📅 December 21, 2025
⏰ 8:00am
📍 Crossings Park, 4 Haig Point Ct
A Hilton Head holiday classic since 1992, the Jingle Jingle Run offers both 5K and 10K races. Runners will make their way over Broad Creek via the Cross Island Expressway, with prizes, refreshments, and music waiting at the finish line.
Every participant receives a long-sleeved race shirt and jingle bells—and festive costumes are highly encouraged. Santa has been known to show up too! Registration details are available on the event website.
Nutcracker 5K
📅 TBD
More event details will be released soon—stay tuned!
Final Thoughts
Hilton Head’s holiday charm isn’t about snow and sleigh bells—it’s about palm fronds, warm breezes, waterfront lights, and Lowcountry hospitality. Whether you’re planning a family vacation, a romantic getaway, or a social-media-ready retreat, SolBlu has the rental to match your vision—and the events to make it unforgettable.
Let us help you book your holiday escape and elevate the experience with curated local tips, event calendars, and tailored stays. The lights are on, the island is ready—it’s your time to shine.
