Road Tripping Through the Mountains of Western Massachusetts and Southern Vermont

It was a last-minute trip; the best ones often are. Neither my daughter Katrina nor I had plans for Labor Day weekend, and our wanderlust was rising, so a road trip made for a perfect spontaneous getaway. Even though it was too early for leaf-peeping, we were drawn to the mountains of Southern New England, knowing that the scenery would be stunning and the region rich with literary lore and artistic attractions.

Day One

We started our journey at Katrina’s home in New York City and drove north on the Taconic State Parkway before taking scenic Route 23 east into Massachusetts and to Route 7 north.

Stockbridge

I had to convince Katrina to stop at the Norman Rockwell Museum. She knew little about the renowned 20th-century illustrator, and, as it turns out, I knew less than I thought I did. While we often think of Rockwell’s work as rife with pigtailed little girls, jovial barbers and moms proffering steaming apple pies, some pieces explored more of-the-moment issues such as desegregation and freedom of speech and religion. Permanent exhibitions include highlights of Rockwell’s most beloved and significant works, many of them among the 323 covers he illustrated for the Saturday Evening Post during a 60-year career that spanned from 1916 to the late 1970s.

For lunch, we sat outdoors at Main Street Café, eating sandwiches and people-watching. Tourists glancing at maps were joined by locals dining with their dogs in tow, greeting the servers by name.

Lenox

Sated, we drove the short distance to The Mount, summer home for a decade of author Edith Wharton, best known for her Pulitzer Prize-winning The Age of Innocence (1920). The classically designed home and its formal gardens bear the imprint of Wharton’s graceful aesthetic, which she championed in numerous books on gardening and design.

Despite her great success as an author—her royalties kept her household flush for years despite her husband’s deteriorating mental health and reckless financial decisions—she believed herself a better gardener than novelist. Having read The House of Mirth and walked through The Mount’s sunken Italian garden, its allée of linden trees and the riot of color that is the formal flower garden, well, I would say that she was blessedly multi-talented.

Williamstown

Continuing on Route 7 north, we arrived in Williamstown, where the small downtown is home to Williams College. There, at the elegant Barn Kitchen and Bar, we enjoyed a dinner of Caesar salad; duck leg confit with braised red cabbage, parsnip puree and Morello cherry gastrique; capped off with a dessert of lime pot de crème. We slept comfortably that night in our modernly styled motel room at Berkshire Valley Inn, situated on a quiet country road.

Day 2

Resuming our drive north, we soon reached Vermont. We would be sleeping that night in Killington, just 85 miles away, so we had plenty of time to meander.

Manchester

In Manchester, we climbed the stairs to the second-story Up for Breakfast and gobbled blueberry buttermilk pancakes and cinnamon sugar-crusted French toast—both topped with Vermont maple syrup, of course. Yum!

Manchester has a host of shops. We got absorbed in the three-story Northshire Bookstore and picked up a bear-emblazoned glass Christmas ornament at Epoch Artisans Gallery. Across the parking lot, we explored Pastime Pinball, a playable museum of pinball machines dating back to a 1947 Gottlieb Humpty Dumpty.

Hildene, the Lincoln family summer home built by President Lincoln’s son Robert, came highly recommended. We were impressed by the grounds and the 1905 Georgian Revival house—and the fact that nearly all of its contents are original to the family.

From Hildene, we took Route 11 east to Route 100 north for a scenic drive to Killington.

Killington

That night’s lodgings, The Snowed Inn, had every bit the mountain lodge vibe you might hope for: pine paneling, sink-into furniture, a double-sided wood fireplace (and a scrumptious homemade breakfast the following day). After a dip in the outdoor hot tub, we dined nearby at Charity’s 1887 Saloon, which features a historic 19th-century bar and perfect French onion soup.

Day 3

What do you do at a ski resort in the offseason? We rode the K-1 gondola to the top of 4,241-foot Killington Peak. Fog enshrouded the mountain when we arrived mid-morning, and it was cold at that elevation. Luckily, Katrina convinced me to wait it out with hot chocolates inside the Peak Lodge, and blue sky emerged later that morning. The views were epic. We took a short hike and numerous selfies with the jaw-dropping background before descending in the gondola.

Before making our way back to Massachusetts that afternoon, we hiked a boardwalk trail through a field of wildflowers to Thundering Brook Falls, a 140-foot cascade in the woods—a recommendation from The Snowed Inn’s manager that we would otherwise have missed.

Woodstock

Not to be confused with New York’s Woodstock of festival fame, Woodstock, Vermont, is a charming small town with a host of galleries and shops (Vermont Flannel is the place to get your plaid wear) where we whiled away an hour before lunch at Mon Vert Café. The real treasure in Woodstock, though, was the pure Vermont maple syrup we purchased at Sugarbush Farm, tucked away on a winding road.

Brattleboro

To expedite our journey south, we hopped on Interstate 91, although Katrina insisted on a short detour to highly rated Nik’s Creemees, a tiny purple shack just a few miles off the highway in Brattleboro. A Vermont specialty, creemees resemble soft serve ice cream. Nik told us he makes his creemees with 10 percent butterfat, so they’re twice as creamy as regular soft serve.

Day 4

Florida, Massachusetts

We had arrived at our motel late the previous night and joined a couple from the South at one of the firepits for a brief chat before retiring for the night. After all, our alarms were set for a predawn wake up.

One of the main reasons I had chosen the Blue Vista Motor Lodge was for the spectacular views it affords of the sunrise over the Berkshire Mountains. The morning was brisk, but the in-room coffee warmed me enough to join Katrina in oohing and aahing over the sky’s changing palette.

North Adams

The final attraction on our road trip was the Massachusetts Museum of Contemporary Art, better known as MASS MoCA, which sprawls across a 24-acre campus in North Adams that was once a textile mill. Part contemporary art museum, part performing arts venue—and a wholly intriguing way to spend a few hours—MASS MoCA exhibits artists both well-known (Anselm Kiefer, James Turrell and Laurie Anderson) and emerging. Although not a collecting museum, it does have long-term exhibitions, including 105 meticulously created large-scale wall drawings by Sol Lewitt on loan until 2043.

Back on main roads, the drive home to New York took only a few hours, which had us questioning why it had taken us so long to make a road trip to New England. We’d be back—soon—we promised, perhaps to join the leaf peepers or to see the mountains blanketed in snow. We knew that whatever the season, the scenery and attractions would be magnificent.