The Mohawk Trail—the name evokes the history of these parts. Thirty miles out of Boston Route 2 heads west, and halfway to the New York border, turns from through-way to winding country road and becomes that Trail. It winds over verdant green knolls and through shallow valleys, alongside the Deerfield River for a time and into the rolling hills of the Berkshires. This is gorgeous countryside, and as we'll quickly find, an area packed with art and culture.
But we also soon discover that the towns of the northern Berkshires are largely disappointing--fairly dismal, still bearing as they do many economic scars and blighted neighborhoods from the shutdown of mills and industry decades ago. Ironically, it's an area of serious art and culture, with more museums packed into the western half of the state than you'd imagine. A two-day stay at The Porches, a 50 room hotel created in 2001 by combining and renovating a row of deserted mill-worker houses allows us time to explore both the fall foliage and natural beauty of the area. N. Adams, where The Porches is located, is home to Mass MoCA, an enormous contemporary art museum carved out of a grouping of deserted brick mill buildings. A huge retrospective of the bold and colorful wall art of conceptualist Sol LeWitt, completed late in 2008, takes up three full floors of a huge building and is a highlight of the museum. 
In nearby (and more charming) Williamstown, MAWC—the Museum at Williams College—houses a gem of a small collection of everything from Renaissance art through Motherwell in a beautiful building. Just south of town, The Clark Institute holds a world-class collection including enough Impressionists to make the d'Orsay envious, and fantastic groupings of American art—Remington, Homer and Singer Sargent; and British—Turner, Constable and Gainsborough. I guess you can do amazing things when you start with a fortune such as that generated by the Singer Sewing Machine Co, which Sterling Clark inherited in the early 1900’s.
Heading south to the lower Berkshires, we go up and over Mount Greylock, the highest point in Massachusetts at 3,491 feet. Both the route up to and down from the summit afford stunning views of the rolling Berkshire Hills and their sugar maple, oak, beech, ash and hemlock forests in just-about full autumnal glory. Common wisdom has it that Columbus Day is the peak for fall foliage, but Sara, the Innkeeper at the Porches said it's just a touch early this year, and should peak the coming week. 
A few miles winding further south down Route 7 brings us to Lennox, a lovely small village as contrasted to the northern towns--seems if you don't have a mill to go desolate, you'll end up better off in the long run. Route 7 then snakes through bright autumn foliage, past picturesque farms and pretty Lake Mahkeenac and into Stockbridge.
Stockbridge itself is a pretty colonial town, full of white clapboard houses, wide lawns and maple trees turning red and gold with the
season. The Red Lion Inn, our home for two nights, is an old coaching inn, dating originally to 1774-full of charm, as well as creaky floors, squeaky hinges and sticky doors. It’s comfortable, with friendly staff, and the best game in town. The wide front porch full of wicker chairs and rockers is THE place to be seen sipping a bloody Mary or long tall cooler on Sunday afternoon. Ambassador Joseph Choate said "If anyone sat long enough on the Red Lion veranda he would see pass everyone worth knowing.” The restaurant is very good--a bit traditional in menu but with a few modern twists. The Caesar salad was one of the best in a long time, and the special of braised shoulder of Lila’s lamb (a local farm) superb.
The Lion's Den, a low ceilinged cellar pub is packed to the gills after dinner, and
shaking and rocking to the driving rhythm of Dick the Fiddler Solberg and the Sun Mountain Band--bass, guitar, banjo and country fiddle. It's obviously mostly a crowd of fans, who know the band and their work, and it's wildly good fun.
The next morni
ng, we head west to the Norman Rockwell Museum, which houses a large collection of his original works, most pieces that were iconic covers of the Saturday Evening Post. To see these large, up close and personal, and admire the detail, craftsmanship and wit that went into them is a real treat. his last studio, in Stockbridge, was moved onto the grounds in 1986, and is preserved as it would have been at his heyday in the early 60's, with a nearly finished Post-covere illustration on the easel.
Nearby Naumkeag, one of the so called gilded-age mansions, designed by Stanford White in 1885 gives a view into country life of the wealthy in that age. Naumkeag is perfectly preserved as it was in 1958 when Mable Choate, the daughter of the builder and last owner and resident died. It's a beautiful period house in a stunning setting in expansive gardens and panoramic view out over the Berkshires. The gardens cover acres, and were the result of a 30-year collaboration betwee
n Mable and noted landscape architect Fletcher Steele. They include an evergreen garden, several terraced lawns, a knotted parterre, walled Japanese garden and the beautiful Blue Staircase, a work renowned in garden design.
Art, music and culture in general are very well represented in the Berkshires. Edith Wharton's estate The Mount, several more historic houses preserved by the Trustees for Reservations, the Berkshire Botanical Garden, The Berkshire Museum, and Tanglewood, summer home of the Boston Symphony are all crowded into this relatively small area, but we'll have to save them for another trip. We've seen wonderful art, and absorbed soul-delighting views in near-prime foliage-time, and are visually satiated and well satisfied.
Restaurants worth a visit:
Gramercy Bistro--No. Adams Contemporary American
Mezze Bistro--Williamstown Contemporary American
Zinc Bistro--Lennox Classic French Bistro food
Red Lion Inn--Stockbridge American Classics with a twist