Riddle Road

Andrew Meunier
May 6
2 min read

Updated: May 10

Greenwich, NY (Washington County)

The southern half of Washington County, NY has long been a playground for dirt road lovers. The Tour of the Battenkill (once a pro/am single-day classic, but more recently a mass start, gran fondo-style event) is one of several cycling events that have used these roads to add challenge and variety to their routes.

Riddle Road is representative of some of the dirt roads in the area. It can be accessed from the north near the Cossayuna general store (with a liquor store and post office housed in the same structure). After a steep pitch on rough gravel, the grade backs off slightly as the road runs parallel to several stone walls and a maple syrup operation.

The last time I rode Riddle, the waning November sun kept ducking behind the height of land to the west, playing tricks on my transition sunglasses. I caught glimpses of the mountains of southern Vermont to the east as I pedaled towards the highest point of the road. There, a gnarled pine cast long shadows and an open field allowed the golden-hour sun to warm me again. A gradual descent brought me to the intersection with Christie Road, where it's worth pausing to enjoy expansive views of the rolling countryside and the distant mountains. On that November day, these were dusted with the season's first snow.