Gregg Russell, Hilton Head: Concerts Under the Liberty Oak

• Concerts: Free, under the Liberty Oak in Harbour Town
• Summer shows: 8 to 9:30 p.m., most weeknights late May to August
• Still to come in 2026: Nov. 27 and Dec. 23, 7:30 to 9 p.m.
• Playground: Next to the Harbour Town parking lot, 140 Lighthouse Road

Gregg Russell has been singing to families under the Liberty Oak in Harbour Town since the 1970s, and for a lot of people his summer-night concerts are what a Hilton Head vacation sounds like. The shows are free. Next to them is the Gregg Russell Harbour Town Playground, named for him, with a tree house built around a big live oak. Together they are the easiest evening in Sea Pines for anyone travelling with kids.

Both are in Harbour Town, a short walk from the lighthouse. The rest of the village is in our Harbour Town guide.

Gregg Russell Concert Schedule for 2026

The concerts follow the season. In 2026 the spring run was three weeks of evening shows from March 30 to April 15, mostly Monday, Wednesday and Friday, 7:30 to 9 p.m. The summer run was the long one: 8 to 9:30 p.m., Monday to Thursday from late May through mid-August, plus Memorial Day weekend and July 4, then three nights a week to the end of August and a last weekend in early September. Two holiday concerts are still ahead, on November 27 and December 23, 7:30 to 9 p.m.

That pattern repeats each year, but the exact dates change, and The Sea Pines Resort posts them on its website each spring. If you searched for the Greg Russell HHI schedule (his name is spelled with two g’s), the resort’s page for the current year is the one to trust.

What a Gregg Russell Concert Is Like

It is a sing-along more than a concert. Russell plays guitar and sings, but most of the evening is games, silly songs and getting the kids involved, with children crowding in close to the stage while parents settle in on the lawn under the moss-hung branches. He has played to more than three million people over more than 40 seasons, long enough to be a tradition families pass down.

The Gregg Russell Harbour Town Playground

The playground sits beside Harbour Town’s main parking lot at 140 Lighthouse Road. Its centrepiece is a tree house that wraps around a large live oak, and around it are nature-themed play areas with swings, slides and things to climb. It works before a concert, after dinner or as a break from the shops, and it costs nothing beyond getting into Sea Pines.

Seeing Gregg Russell in Hilton Head: Getting There

Harbour Town is at the southern end of Sea Pines, a gated community. Unless you own property there, are a resort guest or have a Sea Pines rental reservation, you pay a gate fee to drive in: $10 per day for a standard vehicle. Park in the Harbour Town lot; the playground is right there and the Liberty Oak is nearby.

Around Harbour Town

Make an evening of it: climb the Harbour Town Lighthouse before it closes, walk out on the Harbour Town pier for the sunset, and find dinner in Harbour Town’s restaurants. For the rest of the resort, see our Sea Pines page.