Hincapie Gran Fondo
Where: Greenville, S.C.
When: October 25
How far: 15, 50, or 80 miles
Price: from $80, granfondohincapie.com
Why it's a must: Any race named after George Hincapie, one of the Tour de France's most famous American stars, is bound to be tough (the retired cycling legend is also a participant, so he's gotta keep it interesting). This event's location along the Blue Ridge Foothills guarantees it with three heart-clutching climbs, including one that gains nearly 2000 feet in just four miles. But if you love quiet, rural back-roads and fall foliage, you might reach a zen that will help you tune out your screaming calves. "The peak fall colors paint the hillsides with vast swatches of orange, yellow, and red," says CTS coach Josh Whitmore. "Afterward, you can enjoy a post-ride festival at George Hincapie's Hotel Domestique, with live music, cold beer, and great food," he says.