Travelogue: The Berkshires, Western Massachusetts


We planned a family road trip to the Berkshires–a region so-named for the Berkshire mountain range that dominates Western Massachusetts and which we knew would be beautiful in the fall–long before Hudson was born. It was to be our first trip as a family, a way to ease into traveling with a baby. As luck would have it, we ended up needing to fly to California with Hudson when he was just 8 weeks old and discovered that air travel (where seat restraints are not required for infants) may have actually been easier in these early months… if less scenic.
We left on a Saturday and didn’t make it too far before our first stop; somewhere in the parking lot of a schoolyard in Connecticut we got out to stretch and walk Hudson around among some trees. As he really wasn’t a fan of his car seat (hard to blame him, that view of the back seat isn’t too inspired), and we grew worried that a road trip was the wrong idea. But fortunately, with an arsenal of bottles and pacifiers and calming music, we made it to Lenox, Massachusetts before too long (and with only a moderate amount of, if still incredibly painful, crying). Once he had fallen asleep, however, we didn’t want to stop and chance waking him–so with the exception of a refueling break and a stop to grab a sandwich with the engine running, our parking lot tour was the only sightseeing we did on the way to the Berkshires.
We had booked the cottage at a beautiful inn, Stonover Farm, in Lenox (more on it later this week)–and quickly settled in for the afternoon.


There was a wine and cheese hour around sunset, and after some leg-stretching (and bouncing), we met other guests and sampled some local cheeses over glasses of wine in the main house.


I have to be honest: we are usually the shy, anti-social ones who keep to ourselves at B&Bs, but I really enjoyed talking to the other guests. The inn seemed to draw-in a really interesting, diverse group of people–and I found myself looking forward to having breakfast together the next morning.


That evening, we put Hudson to bed and watched Vicki Christina Barcelona with wine and take-out from Firefly. We thought their burger and the quinoa salad were both delicious. Aron went to pick it and described the decor as a bit Starbucks (ouch)–so we were quite happy to eat-in at our cozy cottage.


After breakfast, we packed up the car (it’s amazing how much we would assemble each day in the name of baby preparedness) and drove north to Williamstown. We had originally thought we would spend the day around nearby Pittsfield–recently described as the Brooklyn of the Berkshires–looking around and checking out Herman Melville-related sights (Arrowhead and the Berkshire Athenaeum). But with Hudson asleep in the backseat (and the realization that “Brooklyn of the Berkshires” might be a bit overreaching), we decided to push on.


Williamstown is the charming home of Williams College (founded in 1791)–a small town with a pretty amazing tradition of art curation and two wonderful art museums: The Clark and the Williams College Museum of Art. The University Library also houses original copies of the four founding documents of the United States (the only place outside of the National Archives).


We started the day–which turned out to be sunny and warm–at Tunnel City Coffee (with coffee roasted locally in North Adams) and then made our way about a mile outside of town to the Clark.


The Clark is a very small museum with an amazing collection of works by familiar names. Sterling and Francine Clark established the museum in the ’50s with a personal collection they had amassed, initially, for pleasure. We enjoyed how manageable–if that’s the right word–visiting the museum was. It didn’t feel too large or overwhelming for what had to be a fairly brief tour.


Our favorite part of the visit may have been the Stone Hill Center, a gallery set up on the hillside, reachable by a series of paths through wooded areas, with great views of the Taconic Range and Green Mountains. The exhibit featured tapestries by El Anatsui, made from the remains of found rum bottles (read the press release about his work), and which filled entire walls with beautiful textures and light. They caught Hudson’s eye, too.



Afterward, famished, we tried a local favorite–Hot Tomatoes–and took our slices of pizza behind the take-out spot to a bench by the river. It was beautiful. And the pizza was delicious. Since moving to the East Coast from California, we’ve noticed that most pizza sold by the slice out here is finished in the oven after you order it, whereas most slices sold out west (that we encountered) seemed to be kept under warming lamps. Why is that? A freshly crisped slice is so much better!

We had planned to drive from Williamstown back to the inn, for happy hour, but Hudson was sound asleep and we couldn’t pass up the opportunity to go out for dinner. He slept in the car seat beside the table for the entirety of our dinner at Alta that evening. In fact, when we told our waiter we’d like to linger with our wine for as long as he would allow–gesturing at the baby–we learned that he wasn’t even aware he was down there.

Our impression of Alta was that its menu tries to be a few too many different things (comfort food, Italian, fusion); but our meal was still delicious–we each had pate to begin and while Aron sampled the duck, I had a dinner-sized portion of one of their salads as a main.

One of the best parts of our stay was waking up to find light streaming into the cottage before walking down to the main house for breakfast. The trees behind the property seemed to get a bit more colorful every day.

Hudson would usually take a nap just after we ate and then we’d head out for the day. Day two took us to the nearby town of Great Barrington, where we found our favorite culinary destination of the trip: Rubiner’s Cheesemongers and it’s adjoining sandwich shop and cafe, Rubi’s–housed in a beautiful, old bank.

After picking out deliciously pungent senne-flade cheese at the grocery, we took a seat in the beautiful, wood-paneled back room to enjoy our lunch. My ham and swiss was wonderful–simple but made with a wonderful, aged-Gruyere and pressed with plenty of butter. We also shared a delicious prosciutto sandwich. Everything featured local ingredients–and the grocery showcased the region as well.

 For dessert, we walked around the corner onto charming Railroad Street to SoCo Creamery. The small-batch ice-cream shop is a local institution that seemed hard to pass up.

In the afternoon, after stopping at a roadside farmstand, we drove into the tiny village of Stockbridge–with its famous (tiny) Main Street, immortalized by its most famous resident, Norman Rockwell. We wanted Hudson to nap in his carrier and decided another museum visit might be just the ticket.We were definitely some of the youngest visitors at the Norman Rockwell museum, which houses a vast collection of the paintings and illustrations that we all recognize from his series of Post covers. His Stockbridge studio has been moved onto the 36-acre site.

On our way back to Lenox, we drove through West Stockbridge to stop at Baldwin & Sons, where they have been making and selling vanilla and other extracts since 1888.

We picked up some provisions in town (including some Great Barrington-roasted coffee at Lenox Coffee) and returned to Stonover just in time for wine and cheese. Everything was aglow by the time we returned–the sun was just setting–and we were looking forward to building a fire. Luckily, the evenings were cold enough to warrant one–even if just barely. For dinner, we had more wine and cheese, especially enjoying fromage blanc with lavendar from Nettle Meadow  with slices of pears from one of our farm-stand stops.

By this time we were settling into our morning routine–and growing worried that we weren’t going to possibly fit in everything we’d like to do in the area. One of our absolute musts was a visit to Mass MOCA, but we neglected to read that the museum is closed on Tuesdays. Thank goodness we had Wednesday as well. We still enjoyed the drive to North Adams after breakfast–so much so that we didn’t completely remind repeating some of it two days in a row.

We followed back roads toward a sign for Lakeview Orchards and found the tastiest cider donuts in an absolutely stunning setting. Had Hudson been awake, we might have gone apple picking there–but instead, I ran in for some sweet snacks while Aron kept the car running.

Believe it or not, we were actually a little disappointed with how perfectly sunny and blue the skies were. Those hills would have looked amazing under the cover of clouds. As it was the color was pretty unreal–amazing.

We found our way to Route 2 and the Mohawk Trail (even if partially closed due to damage from Hurricane Irene), and followed the Deerfield and Cold Rivers to the town of Shelburne–and its seasonal Bridge of Flowers.

After a quick lunch at Cafe Martin on Bridge Street, we wandered over to see the “glacial potholes,” and then I stopped in at Mo’s to pick up some fudge. While our fudge was being wrapped up, I sampled some of the browned butter ice cream and knew I’d made the wrong choice. I still regret leaving without a cone. It turns out that the ice cream is made locally by Herrell’s, in Northampton (and is also served at Lickety Split in Williamstown). Next time.

We drove back into town, passing by Lenox’s lovely Chapel on the Hill, just as the light was getting low and it was reaching that magic hour.

Nudel–the restaurant most often recommended to us prior to our visit–was opening for dinner, and pretty empty yet, so we decided to chance sitting down. Hudson was asleep when we arrived, and more or less patient during our very quick meal.


We may have sped through at a record 45 minutes or so, but somehow we still had enough time to enjoy drinks, an appetizer, and two main dishes. I have been planning to try and recreate the apple salad we had there ever since. With hazelnuts, maple vinaigrette, currants, sage and mint, it was delicious! My pasta–a Pizzichi di Farro with Jerusalem artichoke cream, Gran Padano and Kale, was also memorable.


We vowed that on our next trip, we might do some hiking, biking, or horseback riding, but this trip turned out to be more about scenic drives and art museums–and figuring out how to travel with a baby!

So after picking up more donuts from Lakeview Orchards, we learned that modern art museums (and especially Sol Lewitt Wall drawings) are perfect for 13-week-olds!


Mass MoCA is set in a complex of interconnected, 19th-century mill buildings in North Adams–formerly the site of Sprague Electric. The structure and its history seemed to inform much of what was on view.


Most of the gallery space, however, is devoted to a So LeWitt retrospective: 105 wall drawings installed on three floors for a period of 25 years.


I felt exhausted after the exhibition–it’s so visually stimulating. And it clearly wore out our little baby, who could not take his eyes off the bright colors and high-contrast walls, too.


It was a definite highlight.

We stopped at Mount Greylock Reservation on the way back and took a beautiful drive to the summit for gorgeous views of the valley below. We passed trailheads for the Appalacian trail and I kept picturing Bill Bryson going Into the Woods. The best part was on the way back down when we found an unpaved road, like a carriage-way, back out to Adams. We were surrounded beautiful, golden trees.

We tried once more for a chance at apple picking at Bartlett Orchards, but found that they’re only open to the public on weekends. We picked from among the pecks at their store, instead, and admired the view from their rows of trees.

Our last stop that evening was at Guido’s store in Pitsfield for some local beer–and then we settled in at the cottage by the fire.


We found that the hillsides around Lenox grew more colorful every day we were there and we were so glad to have had almost a full week to witness the change. Had we more time, we might have also added the Shaker museum, Melville’s Arrowhead, or Edith Wharton’s The Mount to our visit. I would have also enjoyed touring the Crane Paper mill. And of course, as we passed by the entrance to Tanglewood every time we turned onto the road to Stonover, it would be nice to visit in the summer and see the Boston Symphony play. We both remarked on how much great culture seemed to thrive in this relatively small area and would love to return.

We drove back home via Great Barrington, stopping once more at Rubi’s for sandwiches (and a ice cream sandwich from Rubiner’s), and instead just tried to soak in as much of the mountain air as possible before returning to the city.
It was a different kind of trip for us–one where an extraordinary portion of our attention was devoted to whether Hudson was asleep, about to fall asleep, or might stay asleep, one where one of us often sat in the back seat juggling pacifiers and dangling toys while the other tried to drive with the right combination of smoothness and “jiggle”; but it was also our first real trip as a family, and that alone was terribly exciting. And I think it was, all told, a big success. I know that’s how I’ll remember it for years to come.

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