Rensselaerville Cycling Festival

Where: Rensselaerville, New York

When: September 28

How far: 25, 55, or 84 miles

Price: from $85, rensselaervillecycling.com

Why it's a must: New to the Gran Fondo calendar this year, the Resselaerville sticks to the criteria by offering a tough course – designed by pro rider and climbing specialist Tyler Wren – with some 9,000 feet of climbing over paved and dirt roads. See if you can hang with Wren and some of his elite teammates, who will ride out with participants at the mass start. If you get dropped, no sweat. There are multiple timed-segments that will analyze how you measured up against the pros later. Sip a glass of Sutter Home wine, a supporting sponsor, afterward as you check your results.