Where: New York City
When: May 18
How far: 50 or 100 miles
Price: from $299, granfondony.com
Why it's a must: Cycling in NYC isn't just for Brooklyn hipsters on fixies and Citibike commuters. This challenging course calls dead-serious, kitted-out road warriors from all over the world The largely international race starts in the Big Apple on the iconic George Washington Bridge and then weaves between New Jersey and New York state lines along hilly streets with lush green trees (expect 3,000 feet and 8,000 feet of climbing per route). If you're good enough to earn "King of the Mountain," you'll go home with a sick new De Rose GFNY Protos road bike equipped with Campagnolo components (a super limited-edition model).