Mt. Tamalpais Hill Climb, Stinson Beach, CA
This 50-year-old race—which brings in 350-plus riders every September—begins with 4 miles of flats along Bolinas Lagoon before rearing up the 4-mile, 1,500-foot ascent on Bolinas-Fairfax Road. The kicker? The last 4 miles offer ever-punchier rollers, officially known as the Seven Sisters—or sometimes the Seven Bitches.
Miles: 12.2
Elevation gain: 2,200 feet
More: 4 Tips for Cycling Uphill
Sunshine Hill Climb Boulder, CO
Sunshine Canyon begins in Boulder and tops out at the historic mining town of Gold Hill. Every May, it's where mega-lunged amateurs line up next to the town's countless pros. Grades average 6.7 percent on the first half of the climb, but surge up to 14 percent in spots. There's a respite that includes flats and a descent before riders hit washboard gravel with switchbacks purported to reach 23 percent—where it's time to either push on, or blow up and turn back.
Miles: 9.1
Elevation gain: 3,226 feet
More: Sitting Vs. Standing When Cycling Uphill
Mt. Ashland Hill Climb Bike Race, Ashland, OR
Thirty years ago, a couple of roadies challenged a couple of mountain bikers up Mt. Ashland from Lithia Park. The roadies took paved Highway 99. The others followed dirt roads past mine shafts and ponderosa pines. They met on the last 2 miles before finishing at the local ski area (6,500 feet). No one remembers who won, but the question of superiority is revisited every September.
Miles: 18 (dirt), 24 (road)
Elevation gain: 4,600 feet
More: Going Uphill Fast With Power
Gear Up for Lyme Mt. Equinox Uphill Bike Climb, Manchester, VT
Scheduled two weeks before the legendary Mt. Washington Auto Road Bicycle Hillclimb, this ride up the highest peak in southern Vermont's Taconic Range is the perfect tune-up for those compact cranksets. It's just as steep, but shorter by a few miles and far less windy. Families cheer for riders along the route and prizes include B&B stays.
Miles: 5.4
Elevation gain: 3,248 feet
More: 7 Tips for Climbing to the Top
Teton Pass Hill Climb, Wilson, WY
Highway 22 traverses an 8,431-foot gap between Jackson's outskirts and Victor, Idaho. In winter, the summit parking lot is packed with backcountry skiers; all summer, cyclists try to outcrawl each other up its exposed 10 percent grades—which alternate with short, lulling flats—for glimpses of the Teton Range. Once a year, in July, you can throw down 20 bucks, meet at Hungry Jack's General Store, and join the official competition.
Miles: 4.7
Elevation gain: 2,284 feet