Small Towns: Chesterfield, MA



The Hampshire County town of Chesterfield, Massachusetts, is an old town that was settled in 1760. Western Mass folks apply the term “hilltown” for a place like Chesterfield that’s perched above the Connecticut River Valley. It also tends to designate a place where once hardscrabble farming took place before those with commonsense stopped shifting rocks and too their plows elsewhere. You’ll see old stone walls in the area from its days of raising Merino sheep, but there are only a handful of farms in Chesterfield now. Mostly its history is reflected in the number of handsome Federal-style buildings that dot what is called Main Road, though it’s really pretty much the road and you have to know where you’re going to wander down a side byway if you’re in any kind of hurry.  




Hurry doesn’t define Chesterfield. It’s one of those places into which people move because they want to slow the pace of life. It’s a pretty close-knit community that still has a town meeting form of government but, in winter, it can be a challenging commute to places such as Northampton (14 miles), Springfield (34 miles), or Hartford (59 miles). Your cellphone probably won’t work in town and the local general store might give you some WiFi connectivity. The only guarantee is inside the town library.





Chesterfield has 1,222 people, a historical peak, but it seems like fewer as they are spread across 31 square miles. There’s a post office in the town center and a historical district on western edge, though the latter–basically an old schoolhouse–is tucked amidst some down-market homes and an abandoned building insulated by piles of garbage. But, as in the case of most hilltowns, locals like each other’s company and visitors looking for some solitude can find a few places to stay. Plan on driving for food, though, as Chesterfield has no restaurants. 




Why would anyone from the outside wish to do that? First of all, it’s a pretty place in the center–almost like what people from far away think of when they conjure an old New England town. If you’re a hiker or just like driving around backroads, you can take in some very pleasant scenery. The main attraction, though is Chesterfield Gorge, a Trustees of Reservations property. Its where the glacier sliced through a notch in the rocks through which the Westfield River rushes. Only those with a death wish would try to paddle it. The picture is from the spring. As you can see from the final photograph, in the fall after a dry summer like that of 2020, you can fill your bathtub and it will be deeper than the Westfield, as seen here a few hundred yards from the Gorge.




In normal years, though, the river further downstream offers pretty good fishing. Anyone passing through the area in spring should definitely make a detour off of Route 9, grab some coffee at the general store, and take a peek at the Gorge. Linger in town if you’re weary.


Rob Weir

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