Nearby, in the postcard-pretty town of Stockbridge — birthplace of Arlo Guthrie’s “Alice’s Restaurant” — the Norman Rockwell Museum is marking its centenary of the artist’s first Saturday Evening Post cover. From 1916’s “Boy with Baby Carriage” comes “Build a Better Baby Carriage,” a kicky show of contemporary sculpture on its lush grounds. Then duck inside “the room where it happened”: Rockwell’s own, perfectly preserved studio.
Hike in the footsteps of literary giants like Herman Melville and Nathaniel Hawthorne, who spent time on the summit of Monument Mountain’s 1,642-foot Squaw Peak outside Great Barringtonin the Berkshires. From the top of cliffs, gaze upon a glorious landscape, including Mount Greylock and New York’s Catskills. Using the Hickey, Squaw Peak and Indian Monument trails from the Route 7 trailhead, hikers can navigate a nearly 3-mile loop along a former carriage road, by a jumbled boulder field and under cliffs. There are some abrupt pitches, but those Housatonic River Valley vistas are worth it. (thetrustees.org)
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To shop at the world’s largest Christmas store, Bronner’s Christmas Wonderland, which takes up two entire football fields, you’ll have to travel to Frankenmuth. Another town with Bavarian roots, Frankenmuth also has a street called Christmas Lane decorated with hundreds of lighted displays, and businesses here go all out when it comes to holiday cheer – you’ll find the streets lined with lighted trees and garlands and other illuminated creatures. Make sure to pay a visit to the Bavarian Inn Lodge where the lobby Christmas tree is hung upside down from the ceiling. This is a very old European tradition that is not often recreated.
They coast into the empty parking spaces like time travelers coming home.
A dusting of fresh snow powders the sidewalk in front of the Red Lion Inn in Stockbridge, and the Berkshires do indeed feel “dreamlike on account of that frosting,” as James Taylor sang in 1969. It’s just frosted enough for atmosphere, too; not enough to keep the vintage cars away. A pale turquoise ’55 Studebaker lumbers into place. Here comes an Oldsmobile Rocket 88, with a Christmas wreath dangling from its pug nose. A pristine ’51 Mercury four-door sports sedan looks as though it’s just driven here from the showroom.
We watch in silence, this first weekend in December, our frozen breath suspended in the air, as these elegant, multi-ton souvenirs pull into their berths. They’ve driven a long way, 60 years or more, sparking admiration and sometimes wistful memories. It’s beginning to look a lot like 1955 … a Norman Rockwell scene, if ever there was one …READ MORE
Tucked into the Berkshire Hills, Stockbridge maintains the rural village sensibility it had back in the 1950s when Norman Rockwell moved to town and painted his iconic images reflecting small-town life for covers of The Saturday Evening Post. Including neighboring West Stockbridge, four miles away down Route 102, one can easily fill a weekend with historic home and museum tours, boutique shopping expeditions, hiking excursions, and fine and casual dining. Located 130 miles west of Boston, the area is a fall foliage hot spot but worth a visit any time of year. Read more
Population: 1,947
Serving as the inspiration for Normal Rockwell’s depictions of Americana on the front page of the Saturday Evening Post, Stockbridge is truly the paradigm of a small New England town. The artist lived in this undeveloped gem in the Berkshires from 1953 until 1978, capturing Stockbridge’s unique character in his paintings. Today, you can visit the Norman Rockwell Museum to see a retrospective of his work; also tourChesterwood, sculptor Daniel Chester French’s summer home. In many ways, Stockbridge feels timeless with its well-preserved architecture from the 18th and 19th centuries, which explains why this has long been a destination for wealthy Bostonians looking for a country escape. What’s more, Rockwell wasn’t the only artist to be inspired by this Massachusetts town; Stockbridge has been immortalized in James Taylor’s “Sweet Baby James,” and in Arlo Guthrie’s classic, droll Thanksgiving monologue-ballad “Alice’s Restaurant.” The town is also home to an eclectic shopping scene and Rouge, a French bistro housed in a shingled cottage just outside of town.
Where to Stay: The Inn at Stockbridge has beautiful grounds, but its proximity to the highway means some rooms are less quiet than others. The Red Lion Inn has been in operation since 1773 and consists of one historic building and nine annexes, each one unique.
Plan Your Trip: Visit Fodor’s Stockbridge
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Massachusetts’ Berkshire County, commonly simply referred to The Berkshires, is a peaceful place. You come to relax, you come to enjoy life, you come to enjoy the scenery. You come to meander.
For good reasons, the region has been a long time fall destination. Located in a perfect mountainous country setting, it is one of the best location to enjoy the symphony of colors that the fall season has to offer.
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On a crisp autumn morning not too long ago, I walked out the front door of my room at the Red Lion Inn just off Main Street and headed in the direction of a forest, where in 10 minutes I’d be hiking along the Housatonic River.
It seemed like a wild idea, exploring the area so freely without four wheels. I was in a small town called Stockbridge in the middle of the Berkshires, a place that had long epitomized car-dependency. My parents had raised me on stories of adventure, including those 1970s Charlemont road trips to a perfect cabin in the woods. I had envisioned their car (I think it was a Volvo station wagon), regularly stocked with wine, beef, and friends, as the way to escape city life. Taking a car never seemed like anything but the only option to get to the Berkshires
“The best of America, the best of New England,” is how the American artist Norman Rockwell characterized the small town of Stockbridge. Sequestered in a green valley, surrounded by the rolling Berkshire Hills, and just 2.5 hours north of New York City and two hours west of Boston, Stockbridge is both a gateway to the great Massachusetts outdoors and one of the region’s cultural hubs. In the summer, the Tanglewood Festival showcases music ranging from choral symphonies to contemporary jazz. And as Christmas approaches, the town’s snow-swathed Main Street celebrates with a range of activities, topped off by a recreation of the 1950s Norman Rockwell painting that fixed the street in the American imagination. Beyond the sparkle of the town rise wooded hills and hikers can use Stockbridge as a launching point for stretches of the Appalachian Trail.