Above the Amenia Hairpin, this lay-by looks over the New York landscape east of the Hudson River.

Snakes employ astonishing methods of locomotion. Legs" Who needs ?em! Using muscles and scales, snakes hug the landscape as they wind along their way. Roads can be like that, with narrow, winding runs of asphalt that hug each rise and bend.

Snaking asphalt brings joy to this motorcycle rider, and east of the Hudson River there?s a region with plenty of it. This area of small towns, farms and woodlands straddles New York?s border with Connecticut and Massachusetts. The rolling landscape means the roads rarely go straight, and with some route planning it?s easy to avoid population centers. Connecting roads with snake-like curves is the inspiration for this ride.
Roughly in the center of this region is the western Massachusetts town of Great Barrington. It has a picturesque, old-fashioned Main Street neighborhood and interesting options for eats, accommodations and entertainment, so it?s a good base of operations for two routes that begin and end there.

Map of the route taken, by Bill Tipton/compartmaps.com.

My friend Andrew joins me and we?re up early to take photographs in the best morning light. Andrew points out the Mahaiwe Performing Arts Center on Castle Street. Berkshire County, the westernmost part of Massachusetts, is renowned as an arts region, and this historic venue has been a performance site since 1905. One marquee is lit up and the neon calls to ...