Massachusetts Route 57

I have taken a lot of road trips this summer: west, south, north. On my way to any place in the first two directions, I’ve tried to explore a territory I call “middle Massachusetts” between the greater Boston area (which I tend to extend to Worcester) and the Berkshires. The latter has a very strong identiy as you can see from the map I found in a shop in Great Barrington, below, as does greater Boston, the North and South Shores, and Cape Cod. But I’m just not sure about the middle: part of it could be called the Connecticut and/or Pioneer valley, but other parts seem not exactly mysterious to me, but rather amorphous. My attempts to discover and characterize Middle Massachusetts has taken me down some small old roads, and so far my favorite route has been Massachusetts Route 57, which extends from just south of Springfield almost to Great Barrington, just north of the Connecticut border. This route is perfect: not one chain store, lots of old houses, general stores, taverns, rolling hills, rivers, state forests, and a lake or two. I’m not sure why it’s not referenced on maps of nineteenth-century Massachusetts turnpikes, as it was clearly a major route from Springfield to the Berkshires from quite early on judging by the structures that line its path.

From the Berkshire perspective above, Route 57 includes several western Massachusetts towns, but I don’t know, Sandisfield doesn’t feel very Berkshirey to me although it is formally in that county. My favorite town on Route 57, Granville, is definitely not a Berkshire town, nor is neighboring Tolland, and then you drive through the New Boston village of Sandisfield, Sandisfield proper, New Marlborough, Monterey, and then finally Great Barrington. Route 57 merges with Route 23, another nice old route but not quite as pristine and rural. Great houses line the road, some a little shabby, some very shiny. Soon I was in New York State, and I returned home on a series of other lesser-known east-west routes, in northern “Middle Massachusetts.” It’s just too easy to take the Mass Pike.

Structures in Granville, West Granville (for some reason I didn’t snap a picture of the very much open Granville General Store—which has great cheese—but I did capture the very closed West Granville Store) New Boston, Sandisfield and New Marlborough along Route 57.

7 responses to “Massachusetts Route 57

  • Katherine Greenough

    Donna — thanks very much for these pictures from your travels. I’ve enjoyed all of them you have sent this summer, and hope I can get out to Route 57 sometime myself. It looks like you had beautiful weather, too.
    Best, Kathy

  • Brian Bixby

    To judge from Wood, the western segment of route 57 was part of the 15th Massachusetts Turnpike from Hartsville westward. The “Book of Berkshire” for 1887, in which towns are listed by their social importance, puts Sandisfield on page 195 out of 222, which means it wasn’t seen as much of a destination back then for summer visitors to the Berkshires. All that said, 57 is a nice, quiet road.

    I once accidentally tripped two burglar alarms in the center of Monterey, one at the town library. But that’s on 23, another nice road, not 57.

  • paull61

    Thanks for showing us a part of Massachusetts that is not so well known. It’s good to know there are still quiet and quaint corners in various parts in New England.

  • Eilene Lyon

    How nice to learn about such an idyllic rural route in Massachusetts. The buildings are delightful!

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