A road trip is a defining exercise in the American experience. Getting in the car and driving is a toast to every one of our forefathers from Lewis and Clark to Jack and Neal. Setting your sights on the Berkshires is a way to capture sweet old Americana and first-rate fall foliage, just a few hours to our north. The ride up will feed you a healthy dose of nostalgia; the cities recede in your rearview mirror, the smells of burning engines and diesel fuel are replaced with the smell of burning wood in outdoor fireplaces. Drive slow if you like or drive fast if that’s your preference, and take advantage of the welcoming road that sees no rush hour traffic, but plenty of nature’s best.
The trip begins where the Island ends. Take the Port Jeff ferry to Bridgeport (about one hour and 20 minutes) where you can finish the last of your work, say farewell to our home shores and sail off the week’s stress. Head north on Route 8. Along the way, honk twice for the boys in overalls in Union City, breathe in that beautiful clean air of Colebrook River Lake and let the lonelier stretches of road bring pause to the conversation and turn thoughts inward. This road is the type that runs fast, straight and hilly and eventually starts to slalom around the lakes of the lower Berkshires. As you engirdle these beautiful bodies of water, stop and take in the vistas. You know you’re getting close when your GPS tells you you’re driving parallel to the likes of Roosterville Lane or Antelope Road. (About two hours from Bridgeport.)
The four main villages of Lee, Lenox, Stockbridge and Great Barrington offer much by way of breezing through quaint shops, art galleries and inventive restaurants concentrating on slow food methodologies. Everywhere, outdoor sculpture punctuates sidewalks and reformed avant-garde SoHo types are sipping wine; you feel smart, healthy and natural just walking these streets. The taste of history is a bonus—sights attest to the area’s roots as Revolutionary-era frontier outposts.
Lee is the smallest of towns, but does offer a handful of sweet shops; four Roslyn ladies met on this writers’ trip enjoyed dinner there at Perigee Restaurant. Lenox is slightly larger, and though Tanglewood, home of the Boston Symphony and the local crown jewel, is closed for the season, there’s still plenty to while away an afternoon. Frelinghuysen Morris House & Studio, the former home of these abstract artists, is 46 acres of American and European paintings, frescoes and sculptures by the likes of Picasso, Léger, Gris and Miró. Shopping is centered on the artsy, funky ladies fashions as in the shops of Tanglewool and Sati. Good eats include Alta, Zinc and Firefly for dinner (lovers of greasy spoons can rejoice at Haven and Shots cafes). In between, sip on coffee and French sweets at Patisserie Lenox. Church Street hosts the various contemporary galleries that close early, but Rumpy’s and The Olde Heritage Tavern (aka: The Heritage) will take you into the relatively late night.
Stockbridge is the former home of Norman Rockwell and it shows in every shop window. The artist’s eponymous museum is located here, on 36 scenic acres that are also home to his son Peter’s bronze and stone sculptures. Sip an afternoon beer at the Red Lion (or come back for a late night at the Lion’s Den) and find plenty of ice cream, bakery delights and handicrafts in the shops. Great Barrington is the largest of the villages and has by far the funkiest flare (think dressed up reformed hippies). It’s where you can shop many (socially responsible) boutiques boasting imports like Japanese antiques, fiber arts, hand-crafted pieces from Africa, the Pacific Rim and South America. Passport not required.
Accommodations abound and range from tiny lakeside B&B’s to former private mansions that have been reformed as public lodgings. But the grand dame in comfort and relaxation has always been Cranwell Resort and Spa, luxurious but laid back, nestled on a private 380 acres. The previously mentioned Roslyn ladies attested to Cranwell’s greatness by calling it home for their annual trips with their husbands. Expect exquisite meals, invoking earthy and rustic tastes in traditional comfort food but with a modern twist (Can you say frenched center-cut veal chop with white polenta, the muenster cheese baked off, and sautéed broccoli rabe?) to fit the rich venue but so fresh and delicately prepared you’ll want seconds. Golf and spa won’t disappoint either. Signature treatments of the latter are all about you. The Grand Mosaic starts with an invigorating, light as air body scrub comprised of ginger, cinnamon, pomegranate seed and pepper (yes, pepper) exfoliator. Knowing how gently these ingredients wake your taste buds, you can imagine what they do for your skin. That’s followed by a warm, calming oil that seeps in deep and becomes a massage from the inside out. And finally, a marshmallow-like foam (sweet, but not sticky) and cocooning in a floating bed (it’s true, you float). For the more traditional types, Cranwell’s S.P.A. is their custom tailored massage. The therapist will meld all known techniques to develop the treatment that works best for all your little spots and is capped off by warm towels enveloping your eyes and ears. When you come to, you feel something like being born again.
Any time to go is a good one, but the very end of September and beginning of October will give you the best glimpse(s) of fall foliage in wide open vistas framed with rolling mountains and pastoral scenes. Heads up culture creatures: the Clark in nearby Williamstown will take down their Pissarro exhibit on October 2, although their famed collection of French impressionists remains on view. Barrington Stage will present an original mounting of Lord of the Flies during the month and the Berkshire Botanical Garden will host the Harvest Festival (October 1-2) displaying autumnal tastes and artisanal crafts in addition to their crisp late bloomers. Berkshire Fishing Club will get you out on exclusive 125+ acre Palmer Brook Lake for largemouth bass, chain pickerel and bluegill and supply everything from the fresh air to the boat and rigging.
Anything wholesome, happy or crunchy. Think variety: Simon & Garfunkel, Indigo Girls, Ray Lamontagne, Ryan Bingham, Tom Waits, Otis Redding.
Alternate route: head around the west way and catch Interstate 95 north. Say a wish as you cross Yankee Doodle Bridge in Norwalk just past exit 16. Grab a thimble-full at Trumbull, pit-stop at the Beardsley Zoological Gardens and wonder about the All American Valley as you get onto Highway 8.
Take the sharp detour through CT or even stop and check out historic Riverton and frequent the homemade bakery stands along the way.
There is a campground in Sandisfield, MA. Or picnic in Tolland State Forest.
Lee premium outlets are within reach. If you really can’t help yourself, visit an outdoor outlet mall not unlike our homegrown version featuring designer shops like Calvin Klein, Cole Haan, Lacoste, Michael Kors and others.
Best for nature lovers, art hounds, theatergoers and collectors of objects from far-flung places. Head up late Thursday afternoon through Sunday to take it in at a chill pace.