Route: Bear Mountain
Distance: 95.2 miles
Fun and challenging routes abound in New York City, but if you're a serious cyclist with a free day, all roads lead to Bear Mountain. The 4.5-mile climb, which averages a 7-percent grade as you wind up 1,103 feet of elevation, is a rite of passage for riders. Locals are known to do hill repeats — for the sweeping Hudson Valley views, PR attempts, and wild, fast descents — and take the Metro North train back to the city from nearby Cold Spring Station. However, the grueling journey home along treasured 9W is a big part of what makes the ride so rewarding, especially if you stop to refuel with a maple bacon donut at Gypsy Donut in Nyack.