What it is: A 36-mile, 10,023-foot ascent of the Haleakala volcano, one of the highest road rides in the world.
Why it’s worth it: Nearly any day of the year, riders can dip a toe in the Pacific Ocean at the start in Paia, Maui, and climb on a well-maintained road through five different alpine ecosystems before topping out at the summit of Maui’s highest volcano. Then, of course, there’s the descent.
How to prep: Donnie Arnoult, who organizes the annual race up Haleakala, says cyclists should be in equivalent shape to ride a century. “It’s more about time in the saddle than the hill climb,” he says. “If you can do a five-hour century, it’s roughly the same.” Because it’s Hawaii, riders often don’t account for bad weather, so expect rain and even snow on the summit. Arnoult, who has ridden Haleakala an estimated 400 times, always packs winter riding gear: arm warmers, tights, jacket, gloves, and a hat. Don’t skimp on snacks, either—the last pit stop is about halfway into the ride, at the Kula Marketplace, although you can refill water at the entrance to Haleakala National Park, with ten miles remaining. Be sure to remember the $8 park entrance fee or you’ll be turned around.