Where the boxcars go
Searching for mythic bridges in the Berkshire Hilltowns
Every destination has a deep cut—a hidden space that’s invisible to the average visitor but brimming with secrets and history. Paris has its catacombs, the Playboy Mansion had The Grotto, and beneath the highlands of the Berkshires, the Hilltowns of Western Massachusetts beckon. Picture the transitional hills between the Pioneer Valley and Route 7 (the road which connects Great Barrington, Lenox, and all the other mountain towns) and imagine nearly 40 villages tucked within the woods and twisted dirt roads that meander through this quiet patch of countryside. That’s what the Hilltowns are—a collection of hidden settlements that feel like they’ve been dropped in the nooks and crannies of a crumpled green duvet. But there’s far more than houses hidden up there.
Deep in the forest of MassWildlife’s Walnut Hill Wildlife Management Area, a pair of enormous stone arch bridges tower 70 feet above the West Branch of the Westfield River. These are the Keystone Arches. Stacked and fortified in 1840, these bridges were a partial answer to a question that befuddled railroad architects—how to get a train over a range of hulking mountains. The first railroad that connected Boston to Albany—the Western Railroad—was half-built at this time. The boundary mountains between Massachusetts and New York presented a literal hurdle for the builders to clear. So they followed the West Branch of the Westfield to one of the lowest high points in the Berkshire Range (1,458 feet) and decided this was where the trains could cross through the mountains. But to ensure safe passage for the trains, the architects knew they would need to erect a lot of crossings over the twisting river.
A stonemason from Stockbridge named Alexander Birnie was brought in to construct 27 bridges along the waterway and ten of them were keystone arch bridges. The term “keystone” refers to a wedge-shaped stone at the center of each arch, which locks all of the other arch pieces in place. (Imagine being the foreman of that construction project: just the thought of it is making me twitchy.) This high stakes bridge-building technique has been used across the world for centuries, with one of the oldest known keystone bridges still looming in China and reputed to have been built around 610 AD!
But what’s most surprising about the Keystone Arches of Western Mass is that some of them are still in use today. These bridges are now under the purview of the CSX freight rail company, which spans the nation. You might have heard about them. The company has been at the center of negotiations led by unionized railroad workers who basically have zero time off from their jobs. A railroad strike became a very real possibility back in September and while the company and union bosses did reach an eleventh hour deal, the grim labor conditions that could inspire a strike remain largely under-addressed and the workers have not approved a deal yet. This labor story was how I initially learned about the Keystone Arches and it was around the time when politicians were bracing for a national railroad strike when I went to find the arches.