Gran Fondo New England
Credit: Getty Images

Where: Providence, RI

When: October 5

How far: 27, 65, or 104 miles

Price: from $75, granfondonewengland.com

Why it's a must: Another rookie by Gran Fondo standards, the year-old event spans three New England states – Rhode Island, Connecticut, and Massachusetts – during peak leaf-peeping season. You can also test yourself and see how you stack up on the timed Strava King of the Mountain climb, end your race, and then watch other cyclists start theirs. "The finish is timed for you to watch the UCI-sanction cyclo-cross races at Roger Williams Park, former site of USA Cycling Cyclo-cross National Championships,"  says pro-level CTS coach Jane Beezer.