Hilton Head Island in a nutshell: Vacationing families connecting—via scents, scenery and seafood—with the second-largest barrier island on the East Coast. And while most of the 2.5 million annual visitors tend to come during warmer months, they miss out on what might be the island's best time of year. After Labor Day and before spring break, the humidity drops, traffic trickles off, crowds thin and temperatures average in the 60s. Folks toss on fleece pullovers to walk the 12 miles of beaches; ride fat-tired, single-speed cruisers along epic bike paths; and hunker down at cozy oyster roasts. Sound good? Grab the Lowcountry winter uniform—flip-flops, khakis and light sweater—and come on out to Hilton Head.
To play Indiana Jones, check out the Indian Shell Ring in Sea Pines. More than 4,000 years ago, Native American settlers are believed to have piled discarded oyster shells in a circle to form low walls around their village, now in the Sea Pines Forest Preserve. And on the island's northern tip you'll find the remains of Fort Mitchel. This moat-lined earthen mound relic of the Civil War was uncovered in the 1970s when construction crews were clearing land for a new restaurant. Today the Old Fort Pub serves up high-end Lowcountry staples like crab cakes with green tomato, sweet pepper relish and stone ground grits. Patrons waiting for a table can head next door for a self-guided tour of the fort remains.
One of the most vibrant local groups is the Gullah, a distinct African-American community that has retained much of its African heritage. To learn more about the Gullah's role in Hilton Head history, head to the Coastal Discovery Museum, then polish off your schooling at Harbour Town with a walk to the top of the Harbour Town Lighthouse. Its walls display historic photos and illustrations detailing Hilton Head's path to the present.
Sea Pines Forest Preserve: 843-363-1872
Old Fort Pub/Fort Mitchel: 65 Skull Creek Dr.
Coastal Discovery Museum: Two locations: 70 Honey Horn Drive and 100 William Hilton Pkwy.; coastaldiscovery.org
Harbour Town Lighthouse: harbourtownlighthouse.com
NOTE: Information may have changed since publication. Please confirm key details before planning your trip.