Rides in and Around Williamstown, Massachusetts

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Williamstown, Massachusetts is an enviable base for cycling. It is situated at the foot of Mt. Greylock—the highest peak in Massachusetts with a perfect road for the 1000 meter climb—and boasts easy access to some of the best riding in the Vermont, Massachusetts, New York tri-state border region. The region is hilly and variously New England woodland, rolling farmland, and bucolic river valleys.

Moreover, the off-bike culture quotient is unparalleled:  a summer theater festival, daily public lectures at Williams College, original copies of the USA founding documents at the Chapin Rare Book Library, minutes from three world renowned art museums, restaurants for all tastes and budgets, and pubs for every aesthetic.

Williamstown is home to The Spoke, a quirky but excellent shop. Paul Rinehart is the owner and has been around cycling all his life, including when he lived in France. He also works as motorcycle neutral support mechanic for Mavic at all USA high level UCI races.

Pack up the bikes and spend a long weekend.

Here is a compendium of us locals’ favorite rides, nothing held back. Or join us on the Tuesday Night Cafe Ride, a brisk paced few hours leaving 4:30pm sharp from Tunnel City Coffee on Spring Street.


Climb Mt. Greylock

This is the classic loop (reverse it for a gentler ascent). Up and back is a quick and concentrated jaunt.
This is the hard way, with a dirt climb. Be ready for sustained 18%+ pitches.
Here is a longer loop that opens with a Greylock climb. The rest of it is plenty challenging and scenic, with several challenging dirt sections.

Short Rides without Dirt Sections

Short Pownal Loop—This is the ride to do if you only have an hour to an hour and a half.

Short Rides with Dirt Sections

Short Northwest Hill Loop—This is the ride to do if you only have an hour to an hour and a half and want to ride on dirt roads.
Middle Pownal Loop*—A wonderful rolling route with substantial dirt sections, one 100 meter section of rough (but road bike rideable).

Medium Rides without Dirt Sections

Hoosic Loop—A classic loop from Williamstown, a climb up Petersburg Pass, lovely farm roads.

Medium Rides with Dirt Sections

Potter Hill Loop—Up Petersburg Pass, some sections of dirt on Potter, rolling roads, a bit of dirt on the way back.

Long Rides without Dirt Sections

Buskirk Loop*—Gorgeous rolling farm roads and a covered bridge.
Kingsley Hill Loop—This ride heads out to legendary Kingsley Hill, one of the steepest paved roads in New England. Short, climbers route.

Long Rides with Dirt Sections

Kelly Stand Century—Rolling farm roads, long sections of dirt, Green Mountain valleys, demanding gravel sections, hard route.
Dubuque Loop—Woodsy old roads, remote feeling, steep grades. Some of the roads used in the D2R2. Hard and excellent.
This is the absolutely most scenic hard and long ride* in the area. The climbs are demanding and the dirt sections are for afficionados of the format. Most of all this loop is beautiful.

*These are my flat-out favorites. Highly recommended.

Best Restaurants

Mezze —Posh (and therefore expensive) American Bistro. Make reservations.

Coyote Flaco—Slightly Upscale Mexican/Spanish/South American fusion. Eat in the dining room or at the festive bar.

Hops & Vines—An eatery in two halves: a white tablecloth dining room with a fancy bar and decent wine and liquor selection on one side, and a benches and long table pub side with craft beers on tap.

Water Street Grill—Pub food serving until 11pm so one of the few late night options.

Spice Root—Indian

Thai Garden—Thai

Chef’s Hat—Greasy spoon diner

Tunnel City Coffee—coffee, cakes, pastries, bagels. This is where the Tuesday Night Ride has convened for over a decade.