Sea Pines Events Calendar: Concerts, Festivals and Holidays

• Next up: Harbour Town Fall Fest, September 27
• Holiday concerts: November 27 and December 23
• Every Tuesday: Farmers & Makers Market to November 24

Most Sea Pines events come back year after year: spring and summer concerts under the Liberty Oak, a shrimp festival in September, a fall festival and Halloween in Harbour Town, a bonfire in the Forest Preserve, and holiday shows to close the year. This page keeps the pattern in one place, with the dates the resort has posted for the rest of 2026.

Most of these are in Harbour Town. Visitors from outside Sea Pines pay the gate fee to get in, $10 per vehicle, and schedules can change, so check the resort’s events calendar the week you go.

Sea Pines Concerts: Gregg Russell Under the Liberty Oak

Gregg Russell’s free sing-along concerts under the Liberty Oak are the best-known event on this list. The 2026 season ran spring shows from late March through RBC Heritage week (7:30 to 9 p.m.), then Monday to Thursday from May 27 to August 13 (8 to 9:30 p.m.), with extra dates over Memorial Day, the Fourth of July, late August and Labor Day weekend.

Two shows are left this year: the day after Thanksgiving, Friday, November 27, and a Christmas show on Wednesday, December 23, both 7:30 to 9 p.m. On both nights the free Sea Pines trolley’s Red route runs from the Greenwood Drive stop to Harbour Town, 4 to 10 p.m. Dinner first at one of the Harbour Town restaurants makes a full evening of it.

The Hilton Head Island Shrimp Festival

The Sea Pines Shrimp Festival takes over the lawn beside the Liberty Oak on a Saturday afternoon each September. The eighth one was September 19, 2026, from 1 to 4 p.m.: all-you-can-eat shrimp cooked by local chefs, beer from more than a dozen breweries, live music and children’s activities. Regular tickets were $79 for adults 21 and over, $59 for under-21s and non-drinkers, and free for children 8 and under. Early-bird tickets for 2026 went on sale in mid-June, so watch for next year’s date around then.

Fall in Harbour Town

Harbour Town Fall Fest is Sunday, September 27, 2026, from 11 a.m. to 6 p.m. The Harbour Town shops hold a sidewalk sale all day, the Carolina Dreamers Car Club shows classic cars from noon to 4, Deas-Guyz plays from 1 to 4, and there are children’s activities over the same hours, along with boat rides and watersports from the marina.

Halloween on the Harbour brings games and trick-or-treating around Harbour Town in the afternoon, 1:30 to 3:30 p.m., with a costume fashion show on the Liberty Oak stage at 2:30. The resort had not posted this year’s date.

The Bonfire in the Forest Preserve

The Sea Pines Forest Preserve Foundation holds its 15th annual Bonfire on Friday, November 13, 2026, from 4:30 to 7:30 p.m. in the Sea Pines Forest Preserve: cocktails, a Lowcountry menu, live music and the fire itself. It is a fundraiser for repair and replacement projects in the preserve, and tickets go on sale in October.

Thanksgiving and the Holidays

Around Thanksgiving the resort runs a family scavenger hunt that starts in Harbour Town at 9 a.m. and sends teams around Sea Pines by bike or car to solve clues; it books ahead. Then come the Gregg Russell holiday shows above, and on New Year’s Eve all three trolley routes run from 4 p.m. to 1 a.m.

Every Week

The Sea Pines farmers market runs every Tuesday through November, 10 a.m. to 2 p.m., at the Shops at Sea Pines Center. The resort’s Forest Preserve wagon ride leaves Heritage Farm on Mondays and Wednesdays at 3:30 p.m. through December 28; it needs a reservation, and children 12 and under ride with an adult. For everything that is not on a calendar, see our guide to Sea Pines activities.