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Summer Drives 2003: Berkshire Loop


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Vermont and Massachusetts

Bennington, Vt., is a small, unpretentious city that welcomes truckers and tourists with equal warmth. Families fill up at the Blue Benn diner on U.S. 7, then cross the street to feed the deer in the Vermont Veterans Home Park. If the Benn is mobbed, try the nearby Northside Diner for savory homefries and a coffee klatch with the old-timers. Heading south, U.S. 7 weaves through narrow valleys, past meadows and rock walls. The land offers up cornfields, apple orchards, antique shops and occasional curiosities such as the idled dog track in Pownal-proof that if you build it, they won’t always come.

Just over the Massachusetts border, the manmade perfection of Williamstown, home of Williams College, is almost a taunt to the deep woods and wind-whipped hilltops around it. “We’ll civilize you yet,” the trim town seems to say. There are enough pillars to rival Athens, and even the college’s parking garage looks like the result of a juried architecture competition. Visit the Williams College Museum of Art (free, 413-597-2429) or check the bill at the Williamstown Theatre Festival (, then grab a takeout pizza at Red Hot Tomatoes. Find out what the college kids are listening to these days at Toonerville Trolley Records in the orange clapboard house with bright yellow trim on Waters Street.

Back on 7, head south and you’ll see signs to Jiminy Peak, a ski resort that celebrates summer nonstop. It’s family-friendly, with swimming, mountain biking, alpine sliding and scenic chairlift rides. The resort-undergoing a major expansion-is a short drive from the trails and the road up Mt. Greylock, at 3,487 feet, the highest point in Massachusetts. Layer up, and hope for a clear day.

Farther south, there’s mini-golf on the left in Pittsfield. Better yet, check to see if the Berkshire Black Bears minor-league baseball team is at home. On the Pittsfield/Lenox line, watch for the Dakota, the right stop for juicy steaks. And check out the Pine Cone Hill outlet store for fine quilts, sheets and curtains.

With your new linens in hand, dream that you’re decorating your own Berkshire “cottage.” That’s what the wealthy turn-of-the-century summer people liked to call the 30-room getaways they built in these parts. Several are visible from the grounds of the Norman Rockwell Museum in Stockbridge, located on a hillside three miles from the center of the quiet village. The small museum welcomes children, who readily relate to the skinned knees, bucktooth grins and open faces portrayed in Rockwell’s work. Walk under the arch in the thick hedge next to the museum and soak up the green valley view. But leave time for Stockbridge, where there aren’t any parking meters and no one seems to mind a bit that the old clock at the First Congregational Church runs a bit slow.

Rest for a moment in the rocking chairs on the shady porch of the Red Lion Inn on Main Street. Then head back the way you came, or take an alternate route in Pittsfield by veering right on Route 9 and then left on Route 8 through Adams and North Adams. This way offers fine views of Mt. Greylock and a look at the rich mill history in the gritty, more muscular towns on this side of the mountain.

For a last stop, visit the Massachusetts Museum of Contemporary Art-a venue for visual art, film and performance-located in North Adams ( It’s an injection of verve to this city on the Hoosic River, though the billboards for Okemo remind you that rustic Vermont is once again near at hand.

LENGTH 100 miles

DRIVE TIME Two hours without stopping, but that would be a crime.

TRY TO AVOID Afternoon rush hour in Pittsfield.

DON’T MISS Drive or hike up 3,491-foot Mt. Greylock, Massachusetts’ tallest peak.

GET OUT OF YOUR CAR Stay in a mansion reborn as the Seven Hills Country Inn in Lenox, next to author Edith Wharton’s home; 800-869-6518,

CONTACTS Berkshire Visitors Bureau, 800-237-5747;