Last year, I went to Maui seeking tropical repose but ended up logging the ride of a lifetime. Friends said that just proves how overwhelming my addiction to cycling is, but the real culprit is the island’s formidable network of roads. The queen is Crater Road, which switchbacks through half a dozen eco-zones on its way from seaside to Mt. Haleakala’s rubbly, 10,023-foot summit. The road is broad and smooth and never steep, so you can spin along and watch banks of clouds unfurl over the Pacific. By my numbers: 90 miles, 10,794 feet elevation gain, 3.5 hours climbing. My wife, who went to the beach instead, just shook her head at me when I finished.

The ride got me wondering about other iconic hill climbs in North America. Of course I know the famous ones—14,240-foot Mt. Evans, New Hampshire’s Mt. Washington, SoCal’s Mt. Baldy—but I wanted to find others. So I called John Summerson, author of The Complete Guide To Climbing (By Bike). Summerson’s book catalogs 144 road climbs in North America ("I've ridden 99 percent of them."), and he’s working on an expanded second edition. “The more of these climbs you ride, the more you want to find,” he told me. “It’s the combination of difficulty, scenery, grade, and climbing history that draws you in.”

When I asked him for his five favorite climbs, his response showed me just how passionate he is about hill climbs. “Just five?” he asked with real agony in his voice. “That’s like putting a gun to my head. People think we don’t have climbs as good as Europe in the US, but they just don’t know where to look.”