The Berkshires Blog

Bike the Berkshires

By Marjorie Cohan and Lewis Cuyler

“The scale of the Berkshires is an exact fit for bicyclists, whose sensuous pace is ideal for full discovery of the county’s understated elegance and its historical and present day cultural richness.  Civilization is never far away from the county’s miles of secondary roads that snake their way through gentle finger-shaped valleys and misty hills.  Just by riding, bicyclists savor sights, sounds and smells in a way unknown to travelers restricted by the confines of a car, “Lewis Cuyler, bike rider in the Berkshire Hills.

The best place to begin is an easy ride. South County offers routes through the five communities of Lenox, Lee, Great Barrington, Stockbridge and Sheffield, all of them offering rolling hills and numerous points of interest. The Southern and Central portions of Berkshire County are part of the Upper Housatonic Valley National Heritage Area (Housatonic Heritage), a region that boasts a rich, diverse identity. Biking is the ideal way to sample this river valley region and to experience its historical, cultural and natural resources. Biking in the fall offers cooler temperatures and a riot of color to enjoy as you traverse the county on two wheels.

Berkshire Bike Path Council (BBPC), in partnership with Housatonic Heritage, Berkshire Regional Planning Commission and the five South County towns – has produced a touring map for cyclists that identify historic landmarks, tourist attractions and cultural destinations in this area.  The South County Touring Map insures that you’ll reach your desired destination, and the accompanying information will enhance the riding experience by identifying important heritage resources along the way.

Begin your ride in picturesque Stockbridge, a town immortalized by Norman Rockwell whose work is preserved at the Norman Rockwell Museum just down the road.   Alternately begin in Lenox then stop at the world renowned Tanglewood Music Center, only a short distance from the town center. From there you can cycle to the Historic Railroad in Lenoxdale.  Riding in Lee you can pass the classic High Lawn and the mills that reflect their industrial history. Cycling through Great Barrington includes the sites of the last battle of Shay‘s Rebellion where rebel farmer’s protested against land taxes and the home of Elizabeth Freeman, the first freed slave in Massachusetts.  Bicycling routes cross the Housatonic River often, but crossing over the covered bridge in Sheffield is a historic highlight.

Rides begin in each of the town centers, where parking and restrooms are available.  Most rides are about 10-15 miles but loops and routes intersect for those interested in longer rides. The map describes the routes indicating cycling challenges.  Rides are predominately on road, some less traveled roads and others on busier roads that are more appropriate for experienced riders.  Helmets are required in Massachusetts for children under 12; however BBPC recommends helmets for ALL cyclists.

The South County Touring map is available at Visitor Centers, Bike Shops, libraries, town halls and other businesses, and may be downloaded as a PDF from  Visit for more bicycling resources.

Looking to RENT a bike while you are here in the Berkshires? Check out these outfitters:

Berkshire Bike & Board – Great Barrington; 413.528.5555;

Plaines Bike, Ski , Snowboard – Pittsfield; 413.499.0294;

Berkshire Outfitters – Adams; 413.743.5900;

Marge has been president of BBPC for the last 11 years, working to build a path from Vermont to CT.

Lew who supported and edited this article is a former Editor of the Transcript and author of Bike Rides in the Berkshire Hills.