The Berkshires’ central city has transformed in the last 10 years, as community efforts have reshaped the downtown. For many years, this has been a city of surprises — the kind of place where you can dip homemade sourdough bread into olive oil and garlic on a cold winter night, in a Lebanese-Italian fusion restaurant in mill country with a sense of humor. The menu begins: ‘Then love was the pearl of his oyster, and Venus rose red out of wine …’

Zumba livens up a Third Thursday street festival in downtown Pittsfield. Zumba livens up a Third Thursday street festival in downtown Pittsfield.

It’s the city where Herman Melville wrote Moby-Dick, and lambs, calves and kid-goats gather at Hancock Shaker Village. And today it’s also the city where Barrington Stage Company premieres new work; the Colonial Theatre has re-opened after half a century and merged with the Berkshire Theatre Group, and they all send plays on to Broadway.

Shakespeare plays live on the downtown common, and The Beacon Cinema and the Berkshire Museum screen contemporary and independent films. And hundreds of people come downtown for Third Thursday celebrations in the summer and fall and the annual 10×10 Festival in February.

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Canoe Meadows

Mass Audubon, the statewide conservation nonprofit, protects four wildlife sanctuaries in the Central and Southern Berkshires. At Canoe Meadows in Pittsfield, flat and easy trails wander along the Housatonic River, sheltering migrating birds and butterflies in the meadow, and otters and turtles along the water (and now and then a bear).


Pittsfield Farmers Market

The year-round Pittsfield Farmers Market has now become the only teen-led market in the region, with Roots Rising, a program that helps teens to work at farms and food pantries throughout the Berkshires. The market welcomes in farmers and artisans together, local coffee roasters and even landscape designers.



Herman Melville and his family were living in the Berkshires, in a farmhouse in Pittsfield, while he wrote ‘Moby-Dick’ in the 1850s. From his desk, he could see the outline of Mount Greylock above the surrounding hills, and it reminded him of a sperm whale’s back in the water, when the whale came up to breathe.


Berkshire Mountain Café

French toast from sourdough chocolate bread, with local maple syrup; cherry pecan French toast with sweetened goat cheese and honey … imagine the possibilities. Aura Whitman, former owner of Café Reva, has joined forces with Berkshire Mountain Bakery’s pizzeria and café — and they are forces of nature.



Writers in residence with the Mastheads program come to the Berkshires for a month of writing, weekly roundtables and events with WordxWord poets in July. They work in five outdoor studios designed by Mastheads founders Tessa Kelly and Chris Parkinson, in honor of five writers who knew these hills in the 19th century.



WordxWord gathers writers to perform their own work live in the Berkshires. They come into coffee shops and museums, and compete in poetry and story slams, picking up the mic without a script. They hold events year-round and a weeklong festival through downtown Pittsfield in August.