Live Music for Kids

One of the best things about Hilton Head is that some of the most memorable kids' experiences on the island are completely free. Every summer evening, families spread out on the lawn at Harbour Town in Sea Pines to watch Gregg Russell perform under the ancient Liberty Oak. He's been doing this for over 40 years — singing songs, telling stories, pulling kids up on stage, and writing their names into his songs on the spot. It's genuinely magical, and it's become a rite of passage for generations of families who vacation here. If you do nothing else on this list, do this.

Over at Shelter Cove Harbour, Shannon Tanner runs a similar show — high-energy, interactive, and completely focused on getting kids involved. Shannon has been entertaining families at Shelter Cove for decades and has the same gift Gregg has for making every kid in the crowd feel like the star of the show. The setting is beautiful, right on the water, and the whole thing has a festive, end-of-summer-evening feel.

Coligny Plaza near the beach hosts a rotating lineup of entertainers throughout the summer — musicians, jugglers, magicians, and performers of all kinds. It's more unpredictable than Gregg or Shannon, but that's part of the fun. Check the Coligny Plaza events calendar before you go to see who's performing. All three venues are free, family-friendly, and best experienced with an ice cream cone in hand.