Big-city smart meets New England natural in an art-rich mountain setting.



You’ve got to slow down when Route 7 leaves behind the wide-open valley of the Housatonic River to enter Great Barrington. The road becomes Railroad Street there, right of way to pedestrians stalled in the crosswalk trying to decide whether to have sushi or chimichangas for dinner. Others carry yoga mats, bags of farmers market produce, books, CDs, double espressos and all the other stuff it’s hard to find in surrounding Berkshire Mountain villages like Stockbridge and Lenox.



Compared with them, Great Barrington (pop. 6,800) is like a big city where you can get anything you want, to borrow the chorus from “Alice’s Restaurant Massacree,” by hometown boy Arlo Guthrie. He was 18 when he wrote the satirical ballad about true events on Thanksgiving Day 1965, when he got arrested for illegally dumping some of Alice’s trash, ultimately making him ineligible for the Vietnam War draft. Trinity Church, former abode of the celebrated Alice, is now the Guthrie Center, a stage for folk music, starting point of the annual “Historic Garbage Trail Walk” and a place for interfaith spiritual exchange in a town where there could be something contrarian in the water.



Or in the food. At the forefront of the big-chain-grocery-store-defying, eat-local movement, Great Barrington is devoted to its family farms, farmers markets and co-op. Berkshire Grown, an organization that promotes the production and marketing of locally grown food, spreads the word with lectures by writers like Michael Pollan (The Omnivore’s Dilemma and most recently Food Rules).



Great Barrington’s latest unconventional endeavor is to mint its own currency, an experiment launched in 2006 aimed at getting people to buy everything—not just food— local. Almost 400 businesses in the area trade BerkShares bills; the 5 BerkShares note features W.E.B. Du Bois, the great African-American author and educator whose boyhood home just west of town is a National Historic Landmark.



Incorporated in 1761, around the same time as Stockbridge and Lenox, Great Barrington, too, attracted rich summer people who built Gilded Age mansions like Searles Castle, now a boarding school. But Great Barrington grew up as a mill and railroad center, its blue-collar ring never excised. About 125 miles from New York City, it attracts a hip crowd from the Big Apple, along with New Englanders and recent immigrants from Asia and Mexico.



“Great Barrington is a small, manageable, economically and ethnically mixed town. That’s what I love about it,” says locally renowned Northeast Public Radio director and commentator Alan Chartock, who proudly lives in a house once owned by one of the judges at the Lizzie Borden trial.



When passenger trains still stopped in town, they brought performers from New York, booked to appear at the Mahaiwe, a vintage 1905 vaudeville theater. Now lovingly restored, it offers a year-round schedule of jazz, rock, dance, lectures and HD broadcasts from London’s National Theater and New York’s Metropolitan Opera. Executive Director Beryl Jolly, who came to Great Barrington from New York’s Public Theater, calls it the Mahaiwe Mix, no categories excluded, for the whole “big mix of people you see walking down Railroad Street.”



Early summer brings the Berkshire International Film Festival to the Triplex Cinema, and classical music performed on historic instruments to the Aston Magna Festival at the Bard College Simon’s Rock campus. Not to mention such famous cultural institutions as Tanglewood, Shakespeare & Company, the Norman Rockwell Museum and Jacob’s Pillow Dance Festival just a country drive away.



Then there’s the frame that nature put around the picture, with 1,642-foot Monument Mountain to the east and the rest of the Berkshires to the west—such cozy mountains! Orchards are sheer walls of pink in the spring, farm fields thick with corn in the summer. Fall leaf-peepers train cameras on golden oaks and crimson maples. Honking geese pass over ice-coated bogs and ponds in the watershed of the Housatonic River. All this, and bagels, too. Arlo got it right. -- Susan Spano



Read how these towns were selected.