Mike Dojc

Craving an Alpine fix? The peaks in North Carolina’s High Country may be less prodigious than those in Aspen, Stowe, or Park City, but the southernmost winter wonderland is just a five-hour drive away.

At Hilton Head, beautiful drives usually mean golf balls soaring over manicured fairways. But for one weekend every fall, motoring becomes the island’s preeminent pastime as hundreds of haute wheels and pristine vintage restorations roll onto South Carolina’s southernmost point.

Journey east on U.S. 78 a half hour past Augusta, and you’ll find yourself clopping through the Carolinas’ equestrian epicenter. This is primo sandy-soiled horse country, where sheikhs with dreams of Derby glory train their prized ponies, and the hottest to-dos are typically thrown in an infield under a tent.