Staff Picks: Getaway Weekend - The Berkshires and the Mohawk Trail

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By Paul Farnsworth

One of the best things about living in the tri-state area during autumn is the spectacular fall foliage that is only a short drive away. You don’t have to drive up to Maine or Vermont to experience New England’s treasures.  While there are plenty of places to go see fall foliage, you really can’t beat the drive up through the Berkshires and the Mohawk Trail in Massachusetts.

I recommend taking the Taconic Parkway out of the city. By the time you get into upper Westchester and Dutchess counties, you can already feel the stress melting away. The Taconic is a windy road through the foothills of the Catskills offering up some great views of foliage on its own.

You will want to get off the Taconic at Route 23 (Exit 88) and head toward Stockbridge, Massachusetts. You will pass through some charming small towns like Hillsdale, Egremont and Great Barrington. It is a mini-antique trail with several quaint shops, restaurants and old-time general stores selling knick-knacks. More adventurous folks might want to go ziplining though through the trees at Catamount Ski Area or hike to the spectacular views of Monument Mountain.

Before you know it, you will arrive in Stockbridge, perhaps the quintessential New England town.  The town was made famous as home to legendary painter Norman Rockwell, who lived there for the last 25 years of his life.  A visit to the Norman Rockwell Museum is a must-stop for any traveling through the Berkshires.  His paintings, especially his covers for the Saturday Evening Post for over 47 years, captured the best of small-town America. "Norman Rockwell is so unique in his vision of the American way of life that there should be a wide berth for him to always exist for all of us who love his images and look for inspiration from them. Stockbridge, Rockwell's home, really has not changed. Steven Spielberg once remarked, “What better setting for a Rockwell museum than his own hometown?"

In Rockwell's obituary, The New York Times described Stockbridge as a “picturesque village in the Berkshires that could well have been designed by Mr. Rockwell himself.” In fact, Stockbridge's Main Street looks almost exactly as it did when Rockwell painted it at Christmastime in the 50s and 60s. Stroll the shops where you can buy candles, penny candy and the odds and ends that make your own home a wonderful place.

In Rockwell’s painting, as in real life, Stockbridge is anchored by the incomparable Red Lion Inn. The Red Lion Inn is a magical hotel, and I recommend staying the night here. Built in 1773 as a tavern, walking into the Red Lion is like taking a step back in time.  Start by just sitting in one of the rocking chairs on the porch, having a drink and watching the world go by. You will soon forget any of the stresses of the work week.  Taste a legendary bloody Mary at Widow Bingham’s Tavern, have dinner in the elegant dining room and check out the live music downstairs at the Lion’s Den Pub.  At any one of them, you will feel like been transported back to another century.

After a great night in Stockbridge, head over to nearby Lenox for breakfast. Lenox, best known as the site of Tanglewood - summer home of the Boston Symphony Orchestra - has many cafés and bistros to grab something for the upcoming ride.  Keep your eyes open, you might be in line at the coffee shop next to singer James Taylor, who lives in town.

You will want to take Route 7 from Lenox up to Williamstown and the start of the Mohawk Trail.  The 34.4-mile stretch to Greenfield is home to perhaps the best foliage in the world. Here are some of the highlights as you head east on Route 2.

Mass MoCA - Route 2 takes you right through North Adams and the vast historic mill complex that now houses the Massachusetts Museum of Contemporary Art, or Mass MoCA for short. MASS MoCA is a fabulous complex that presents art exhibitions, music, dance, theater and multimedia events. 

Hairpin Turn - Route 2 is an old trail Native Americans of the Five Nations used to pass between the Connecticut and Hudson Valleys.  One really cool spot is the Hairpin Turn just outside of North Adams. If the 180-degree turn isn’t enough, you can check out the panoramic views of Berkshire mountains and hills and the pleasingly rural Hoosac Valley from the observation point at 1,700 feet above sea level. There is also the Golden Eagle Restaurant if you are looking for a bite to eat.

Hail to the Sunrise - Another must stop along the trail is the “Hail to the Sunrise” statue at Mohawk Park, a statue made in tribute to Native American heritage. The statue was created by sculptor Joseph Pollia in 1932 and the monument honors the peoples of the five Mohawk Nations.

Gift Shops - The Native American theme runs across the Mohawk Trail and there are couple of touristy gift shops with totem poles, teepees and Indian statues. I love them. They are run by good people and have great moccasins, maple syrup and jewelry. Have fun, check them out, have your picture taken with a stuffed bear. 

Bridge of Flowers - Perhaps the highlight of any trip to the Mohawk Trail is the world-famous Bridge of Flowers, which connects the towns of Shelburne and Buckland. The former trolley bridge that is planted with over 500 varieties of flowers, vines and shrubs. Both towns are also fantastic places to stretch your legs.

Shelburne Falls - Enjoy the scenery and get some fresh air at Goodnow’s Chip and Putt Golf Course or get some fried dough, fresh-made doughnuts, and pumpkins and gourdes at Hager’s Farm Market.  Get the friend dough with the maple cream…trust me on this.


By the time you get to Greenfield and Route 91, you will have a decision to make.  Go north and check out Vermont, continue east on Route 2 to Boston, or go south and travel through the Pioneer Valley of Western Massachusetts.  Or you could retrace your steps and go back home via the way you came and hit spots you may have missed the first time.  The great thing about the Mohawk Trail is it looks different depending on the time of day you drive it and the direction you are going in, so retracing your route can be just as enjoyable the second time around.  The peak fall foliage season only lasts a couple weeks but this area is a spectacular place to visit any time of year. 


Photo credit: Norman Rockwell Museum, Mass MoCA, Paul Farnsworth

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