The Oregon Trail

As Route 2 speeds down into the Connecticut River Valley, it veers along I-91 just long enough to skirt the county seat of Greenfield, a place once known for its cutlery, tap-and-die, and other metals-related manufacturing. The proximity of the interstate has endowed Greenfield with some of the few chain motels in western Massachusetts, but it also supports the warm hospitality of the People’s Pint (24 Federal St., 413/773-0333), serving up good food and pints of New England’s most interesting locally-brewed beer.

A world away from the modern interstate aesthetic, but just three miles south of Greenfield along Route 5, Historic Deerfield (daily Apr.-Nov., weekends Dec.-Mar., $18) is an immaculately preserved ensemble of architecture and agriculture dating back over 300 years. More than a dozen clapboard buildings, shaded by a canopy of stately old elm trees, form a mile-long reminder of the time when this part of Massachusetts formed the western frontier of “civilization,” and English settlers waged bloody war against the native Pocumtuck people. The adjacent town of Deerfield, and the famous Deerfield Academy prep school, hardly intrude, leaving Historic Deerfield to stand as it was—fanlight windows, wrought iron, well-worn stones and all. Inside each house, guides discuss the lives, belongings, and historical contexts of the former inhabitants, often with such parental intimacy that you half-expect these long-dead Ebenezers, Jonathans, and Marys to be napping upstairs. One of the finest surviving colonial townscapes in America, Historic Deerfield is well worth a visit, no matter how brief.

Historic Deerfield also offers the Flynt Center of Early New England Life at the edge of a field behind Main Street. The 27,000-square-foot museum, designed to look like a colonial tobacco barn, displays thousands of “fancy goods” and other consumer treasures—pewter teapots, silk waistcoats, and the like—that were keys to civilized life here on the edge of wilderness. For the full historic experience, stay for dinner or overnight at the Deerfield Inn (413/774-5587, $195 and up), right in the historic core.

It’s outside the historic core of Deerfield, and not technically in the Berkshires for that matter, but one of New England’s great beer-makers, Berkshire Brewing Company (12 Railroad St., 413/665-6600), offers tours and tastings in South Deerfield.

Map of the Oregon Trail Route in Massachusetts

Map of the Oregon Trail through Massachusetts.
Map of the Oregon Trail through Massachusetts.

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