For an island of only thirty thousand people, Hilton Head has a surprisingly large entertainment selection. The main attractions are the Hilton Head Symphony Orchestra, offering 10 different concert programs throughout the year, and the Arts Center of Coastal Carolina, which hosts an array of plays, music concerts and dance performances. However, they are by no means the only shows in town. There are several other theater opportunities including the Lean Ensemble Theater, which stages several play productions a year in the Main Street Theatre, the Southeastern Summer Theatre, the Main Street Youth Theatre, and the May River Theatre Company in Old Town Bluffton.

Hilton Head Island is the host to several top flight musical competitions: The HHSO Youth Concerto Competition, which takes place annually at the end of January, and the Hilton Head International Piano Competition during the early weeks of March. The Jazz Corner is a 99 seat restaurant/ jazz club in the Village at Wexford featuring notable combos and vocalists from the region, including visits from grammy nominated artists. Chamber Music Charleston provides intimate concerts at All Saints Episcopal Church several evenings each year. And the Hilton Head Choral Society, a 100 voice ensemble plus instrumentalists, presents 4 major programs per season. Additionally, the Barbershoppers, an a cappella group, provides one performance a year, as well as private bookings and the Hilton Head Dance School & Theatre puts on several dance performances annually.

Also worth mentioning are the 3 movie theatres on the island, one of which, Coligny Theater, is a single screen indie art film house aimed at an upscale adult audience.