Whether you’re a snowbird looking to escape the cold or a family planning a festive getaway, Hilton Head Island is the perfect setting to help you get ready for the holiday season! From dazzling light displays to family-friendly festivals and annual events, the Lowcountry shines bright this season. Below are some event recommendations to guide your stay in one of our many Hilton Head vacation rentals.
Thanksgiving Turkey Trot
When: Thanksgiving Day! November 27th, 2025 | Where: Dockside / Hudson’s Restaurant area, 397 Squire Pope Rd, Hilton Head Island, SC
Kick-off the holiday season with a beloved Island tradition – the Hilton Head Turkey Trot. This festive 5K and Fun Walk welcomes runners and walkers of all ages to gather at Dockside and Hudson’s, winding through a scenic Lowcountry course. Families, friends, and even costumed turkeys join in the fun, creating a joyful atmosphere before the holiday feast. Participants receive a race shirt and medal, with prizes and post-race celebrations adding to the excitement. The Turkey Trot also supports the local community, encouraging donations for The Deep Well Project’s holiday food drive.
Holiday Events in Sea Pines:
Harbour Town Lights
When: November 28th, 2025 – January 1st, 2026 | Where: Harbour Town
Take a leisurely walk along the harbor, reveling in the glow of seasonal figures, with the magnificent Christmas tree as the centerpiece. Harbour Town is the ultimate destination for a festive family experience, offering a lively atmosphere with various activities and live entertainment. The official tree lighting is scheduled right before the Gregg Russell concert at 7:30 pm on Friday, November 28th. As you immerse yourself in the holiday spirit, contribute to the Deep Well Project’s meaningful cause by donating canned goods or a new, unwrapped child’s toy at the Liberty Oak stage well.
Polar Bear Swim
When: December 30th, 2025 | Where: Harbour Town Pool
Embrace your adventurous spirit and join fellow “polar bears” for a refreshing plunge into the Harbour Town Pool on a crisp winter day. Afterward, warm up with indulgent hot chocolate and delightful refreshments.
Holiday Fun in Harbour Town
When: December 27th-28th, 2025 | Where: Harbour Town
Gather at the Liberty Oak for an enchanting evening of classic holiday movies, marshmallow roasting, and delightful train rides. The movie and marshmallow roasting festivities commence at 6 pm, and admission is complimentary with the donation of a canned food item for the Deep Well Project. Experience the joy of train rides for $6 per passenger. Join us for a heartwarming celebration that combines the magic of movies, the warmth of roasting marshmallows, and the joy of a festive train ride.
Polar Pines Express Holiday Wagon Ride
When: December 20th, 2025 | Where: Heritage Farms
Hop aboard our merry wagon brimming with holiday delight! Be part of our journey to our enchanting “North Pole,” where a world of crafts, activities, hot chocolate, and treats awaits. While on the ride, sing along to festive tunes and enjoy the timeless tale of “The Polar Express.” Hop on the wagon starting at 10:00am. If you want to enjoy this jolly ride, reservations are required and tickets can be purchased for adults and children using the link below.
New Year’s Eve Celebration
When: December 31st, 2025 | Where: Harbour Town
Celebrate the New Year with us at the festive ball drop from the summit of the Harbour Town Lighthouse! Indulge in food, entertainment, and live music scattered across Harbour Town. Join the countdown to the ball drop, marking the new year’s arrival with two spectacular moments: 7 p.m. and midnight.
View Hilton Head rentals located within walking distance to these events in Sea Pines and Harbour Town.
Holiday Events Near North & South Forest Beach
Hilton Head Official Tree Lighting
When: December 5th, 2025 (5:00pm- 8:00pm) | Where: Lowcountry Celebration Park
Join the Hilton Head community in the Coligny Beach area at Celebration Park, for the Town’s official Christmas Tree Lighting. This free, family-friendly event includes live music, visits with Santa, hot chocolate, and even an outdoor holiday movie on the big screen. Lawn chairs and blankets are welcome to enjoy a cozy evening as the 30-foot tree is lit, and the park glows with festive lights and holiday cheer.
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Holiday Events Near Palmetto Dunes:
Winter Wonderland
When: December 6th, 2025 | Where: Shelter Cove Park
Join us at Shelter Cove Community Park for the Winter Wonderland Festival, a joyous celebration from 3 to 6 p.m. This free annual event is the perfect setting for families to kick off their holiday festivities! All are invited to enjoy bounce houses, a DJ, a golden candy cane hunt, and more family fun. Admission is free, and donations are appreciated. Treat yourself to concessions, trampoline bungee, and the rock wall, which are available for separate purchase. Come one, come all, and let’s make this holiday season magical!
Shelter Cove Harbour Lights
When: December 1 – 31st, 2025 (After Dusk) | Where: Shelter Cove Harbour & Marina (Palmetto Dunes)
For a romantic stroll, or a fun family outing by the water, the Holiday Lights Display at Shelter Cove Harbour & Marina is a must. Throughout December, the entire harbour transforms into a coastal winter wonderland, with over 100,000 lights twinkling on the water! Stroll along the marina, shop in the harbour’s boutiques, and enjoy waterfront dining while taking in the decorated boats, beautifully lit palm trees and holiday displays. Be sure to catch Santa’s first appearance Friday, November 28th – the day after Thanksgiving for Santa & Shopping Day.
Festival of Trees
When: November 21st, 2025 – December 6th | Where:One Hotel Circle, Hilton Head Island
One of the largest holiday traditions in Hilton Head, the Festival of Trees features a dazzling display of decorated trees and Christmas wreaths. Each year, beginning on the 3rd Friday of November, and running for 16 days, the festival showcases dozens of trees uniquely crafted by local businesses, schools, and organizations. Spectators can visit at anytime to admire the items on display, purchase decor items, or even select a tree. All proceeds benefit Hilton Head Prep’s tuition assistance fund.
View vacation rental homes and villas conveniently located near Palmetto Dunes holiday events.
Other Nearby Events:
Bluffton Christmas Tree Lighting & Parade
When: December 6th –7th , 2025 | Where: Martin Family Park
Just over the bridge in Bluffton, the 54th annual Bluffton Christmas Parade is set to take place. On Saturday, December 6, at 10am, the parade will wind through Bluffton’s Historic District. Festive celebrations continue with the Tree Lighting ceremony on Friday, December 5th, starting at 5:30 p.m. at Martin Family Park, accompanied by caroling and holiday cheer. Following this, kids can meet Santa at Santa’s Workshop (DuBois Park’s Pavilion) and view an outdoor screening of the movie “Arthur Christmas” at 6:30 p.m. under the stars in Martin Family Park. Bring your blankets and chairs for a cozy experience. These events, including the Christmas tree lighting, Santa’s workshop, and parade, mark the official commencement of Bluffton’s holiday season.
Book your Hilton Head Vacation Rental for the Holiday Season
It’s not too late to book one of our Hilton Head vacation rentals for the holiday season! Browse our Hilton Head vacation rentals and find the perfect rental for you and your family, whether it’s just a short stay or looking to snowbird with us in the Lowcountry. Book your rental and enjoy all the festivities Hilton Head has to offer!
