Boston,  Roadtrip

Berkshires Family Itinerary

The Berkshires is a general term applied to the hills and valleys running along the western edge of Massachusetts. They are oddly sophisticated with grand old hotels and great mansions like Edith Wharton’s The Mount. There are swimming holes, orchards, museums, and lots of long beautiful country roads that smell like damp woods and the rushing wind. Joe and I had been wishing for a couple days there with the girls for a long time, and finally things fell into place.

We drove out from Boston Thursday evening arriving at the Porches Inn, the hotel across the street from Mass MOCA around 9pm. Weekday nights run about $80 cheaper than weekend nights at Porches ($300 total). We had requested a pack n play and a pullout couch for our room–both were already set up as beds for the girls–lovely! It was pouring rain and pitch dark but we decided to show the girls the hot tub anyway. The four of us sat in there with our hair getting soaking wet from the rain, and it felt like such a family memory, I loved it.

Thursday night Back in the room we gave the girls a quick warm shower, tucked them in, and closed the dividing doors that conveniently allowed Joe and me to keep our nightstand lights on. I filled out the form for our breakfast delivery– a newspaper, two hot chocolates, two coffees, two muffins, two chocolate croissants to be delivered at 7:45pm. Obviously I fell asleep dreaming of the prospect.

Friday morning We ate up our wonderful delivery, surveyed the view from the porch, played in the pool for a bit, visited the breakfast room for a few more snacks (open until 10am) and then packed up so we could head over to the museum.

Mass MOCA admission for kids under 5 is free, $17.50 for each adult. We quickly split up as Joan wanted to “go outside” (fortunately there were exhibits out there as well) and Lux was entranced by the huge Sol LeWitt walls. Lux must have spent a good half of her tour repeating “We’re coming back here and next time I’m bringing my camera.” We reunited and stopped by the Art Bar, a bright cheerful room of free craft options for kids on the second floor. It had a genius structure to it–pick one of their crafts based on the exhibits, and they hand you a shoebox full of the necessary supplies.

Friday afternoon Pulling out of MOCA we routed a twenty minute drive to Cricket Creek Farm. To drive to Cricket Creek Farm we passed through Williamstown where we could have stopped at the Clark, or poked around the cute town. I can see a nice with-kids itinerary spending two nights at Porches, with one day for MOCA, and one day for the Clark. Passing plenty of cows along the way, we found the little farm store selling cheeses and raw milk, one of my favorite things to pick up on weekend adventures. It was a serve-yourself store, and the animals to be seen were far-apart and sparse. I guess I’ve grown spoiled by the ease of encountering farm animals at near-Boston locations like Drumlin Farm or Russell Orchards. Still, it was a happy stop for us, the milk was dee-licious and my ultimate goal was to break up the driving = success.

After the farm we routed a twenty-five minute drive to Lake View Orchard. This huge orchard allows you to pull your car directly up to the raspberry fields or cherry trees, a BIG perk when picking with kids. Joan had fallen asleep so Lux and I hopped out and picked together, mixing black berries and red raspberries. It was hot in the sun but I loved the views of the rolling valleys and Mt. Greylock. Joan woke up before we left and got to pick a pint of berries, meanwhile Lux busied herself with eating her entire pint.

Friday late afternoon Now we were just an hour drive’s north of Great Barrington, our town for the night. I had hoped to stop at Chesterwood in Stockbridge (admission $17.50/adults), the summer home of a sculptor that looked lovely, with lots of semi-finished figure studies for the girls to examine with an intact track that the sculptor used to move marble around, a topic I knew Joe would enjoy expounding on. But after carefully reading my mom-energy-meter I realized we only had capacity for dinner at this point.

This ended up being ideal timing because we got to Bistro Box at 5pm, before the dinner rush. I could feel the girls’ relief at the sight of the huge lawn and picnic tables as we pulled in to this roadside eatery. We ordered heavy on the grilled items. Our “box burgers” with bacon jam were crazy good. I have had a lot of things called bacon jam but nothing as savory and sweet as that. The onion rings were so crunchy and fresh too. After the girls finished their hot dogs we ordered a special birthday strawberry n sprinkles ice cream cone for Lux that was enormous. I had been tempted to lure us into driving the few minutes back into G.B. for SoCo Creamery because it’s that good, but I’m glad we stuck with the green shady lawn. Sigh…the itinerary-building partner must always be suppressing just one more good idea from ruining the day, no?

Friday night From there it was just a fifteen minute drive to our motel for the evening. The Briarcliff Motel was a standard roadside motel with plenty of stylish elements. For $250 we got two double beds, plus a pack n play that was set up on our arrival. The room itself felt like a classic motel, a bit small for the four of us. But everything felt very clean, tidy, and finished with an eye for details. That evening we enjoyed the outdoor gas fireplace surrounded by daisies and comfortable chairs. And the next morning the amazing homemade breakfast in the lobby: scones, banana bread, homemade granola with local yogurt, and plenty of coffee. Honestly, an included breakfast goes a long way with me. I looked around the G.B. area for awhile trying to find something worth the money, including Airbnb, but I didn’t find anything better. Many spots in the area (the Red Lion Inn, for example) jump their prices by $100 for weekend nights, and require two night stays. I’d be curious to hear any recommendations?

Saturday After breakfast we packed up and drove into G.B. to stock our picnic supplies at Rubiner’s. The cheese shop doesn’t open until 10am so we went to their cafe around the back for a supplementary cappuccino while we waited.

Joan dips her fingers in all my drinks–alcoholic, caffeinated, all of them–which I justify by dreaming of her food critic status someday. At Rubiner’s we picked up a few cheeses, some boquerones anchovies that I only seem to find once a year in random places, crackers, a half pound of salami, and a gourmet fun dip??? I was amazed, the girls were wide-eyed, and sour sugar was had by everyone. Thank you Quin for making that and Rubiner’s for stocking it.

Saturday, 10:20am With just a twenty minute drive to Tanglewood, it made us only 10 minutes late for the morning rehearsal. Lawn tickets are priced about the same for rehearsals as typical evening shows (kids free; adults $13). Lawn tickets can almost always be purchased at the box office at the time of the show, so they are lovely and no-stress. Lawn tickets mean picnicking and music, grass and stretching your legs. Children under 5 are asked to sit towards the back of the lawn, and they are pretty serious about that request. The good part of that is you really feel comfortable listening, talking, and interacting with your kids at standard volumes. We set up our blanket in a shady spot. After about an hour of the show we wandered back to the “kids’ corner” which had two different craft tables set up. Lux was sucked into both of them. Joe and I debated if we were grateful to the crafts–they were fun and a neat memory for her–or resentful since it pulled us away from the music and our picnic blanket for 40 minutes.

After the show we decided to drive back to Boston though I had hoped for a quick stop at Bish Bash Falls. We hit afternoon traffic on the highway and lamented that we hadn’t fit in one more activity. However we got back to Boston in time for dinner and an easy bedtime transition, so I think it might have been worth it! If you were leaving in the morning, I would definitely stop by the Eric Carle Museum of Picture Book Art on your way back.



  • Deanna

    What a lovely summer get away! The first part of your journey holds a very special place in my heart as we were married at Mass MoCA and most of our family & guests stayed at Porches during the wedding weekend! I love all the other stops along the way! We’ve been daydreaming of a trip out the Tanglewood with the kids for a while now. You’ve inspired me to make it happen!

  • beaktweets

    Sounds so perfectly summery! Thanks for sharing. Every year I am reminded of how well you guys live up the summer life.

  • Julie

    We’ve been going to the Berkshires for AGES, but your itinerary is full of new-to-me stuff! Can’t wait to check out BistroBox, Bish Bash, and Chesterwood (even though you all didn’t make it there this visit). So happy you all had such a great time. This is one of my favorite areas!

  • Jess

    Hey Rachel, I really like stopping by your blog – it’s a lovely slice of another life. I just wanted to say that I can completely empathise with this: Sigh…the itinerary-building partner must always be suppressing just one more good idea from ruining the day, no?

    A fellow itinerary-builder, right here 🙂

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