Compared to the carefully preserved Norman Rockwell simplicity of many of the surrounding small towns, the aging industrial cityscape of Pittsfield (pop. 48,000) has made it the place most Berkshire weekenders strenuously try to avoid, despite the fact that its size and the valley’s topography make this nearly impossible unless you have a resident’s familiarity with the backroads.
Despite Pittsfield’s anything-but-quaint appearance, there are actually some good reasons to pay the place a visit. Head out to Holmes Road, at the city’s rural southern edge, and maybe you will see the resemblance between a leviathan and the imposing outline of Mt. Greylock, particularly if you view it from the study window of Herman Melville’s Arrowhead (daily in summer; $10; 413/442-1793). That salty masterpiece, Moby Dick, was indeed written in this landlocked locale, where Melville moved in 1850 to be near his mentor, Nathaniel Hawthorne. While foremost a literary shrine, the spacious farm is also home to the Berkshire County Historical Society, whose well-curated exhibits are always interesting. Serious pilgrims on the path of Ishmael and the great white whale will also want to visit the Melville Memorial Room on the upper level of the Berkshire Athenaeum, Pittsfield’s public library.
As with its other attractions, Pittsfield has some real out-of-the-way gems when it comes to food. In the acute angle between East and Elm Streets at 503 East Street, for example, is the semicircular facade of the Pittsfield Rye Bakery (413/443-9141), a 1950s flying saucer of glass and blue tile with big bright cases of fresh muffins, bagels, and breads beckoning within. For excellent pasta, pizza, and pub grub at a great small-town price, step around the corner to the East Side Cafe (413/447-9405), at 378 Newell Street, a neighborhood bar whose comfort food and convivial atmosphere attract a family clientele.
Places to stay include a large Holiday Inn Crowne Plaza ($119 and up; 413/499-2000) at 1 West Street and other chains, plus the pleasant Berkshire Inn ($75 and up; 413/443-3000), on US-20 a half mile west of US-7 at 150 W. Housatonic Street.
