Episode # 101 – Looking back wistfully: The Berkshires

Over the years, we’ve spent several summer holidays – and one winter holiday – in the Berkshires, staying on various visits in Great Barrington, Stockbridge, Lenox, and Lee. We love the landscape. We love the historic homes. We love the food. We love the absence of high-rises and hotel and restaurant chains. Most of all, we love the summer theatre and music scene.

We like nothing better than sharing our favourite places with our family and friends, so in 2015 we invited Ted’s brother and his wife to join us for a week in the Berkshires. We had previously shared Nashville Tennessee, Branson Missouri, and the Massanutten Mountain region of Virginia with them.

This post is particularly poignant for me, since, as I write it, my brother-in-law is dying. With COVID-19, we will not even be able to make a last visit to see him in palliative care; perhaps it is a blessing that my last memories of him will be enjoying a glass of his favourite red wine as we Skyped and reminisced about travelling.

My brother-in-law loved music, and my sister-in-law is a big fan of live theatre, so I was excited to plan a full schedule of entertainment for us. The only thing they don’t particularly enjoy as a couple is classical music, so we avoided what is one of Ted’s and my favourite summer events: the Tanglewood Music Festival. (If this blog inspires you to visit The Berkshires, I’d highly recommend Tanglewood – not only is the selection of solo, ensemble and orchestral music across many genres incredible, but the acres and acres of park setting is spectacular. The fireworks after performances of Tchaikovsky’s 1812 Overture are especially breathtaking.)

For us, a single week in this gorgeous part of Massachusetts is nowhere near long enough, but we tried to cram in as many activities as possible, while showing off a bit of each of the unique towns that make up the area.

A portion of downtown Stockbridge (above), looking exactly like the Norman Rockwell painting that it inspired, with the exception of the missing vintage automobiles.
Theresa’s Stockbridge Cafe is housed in the original “Alice’s Restaurant”, referenced in Arlo Guthrie’s famous song. Old folkies (like us) get a kick out of eating there because of that connection; others eat there just because the food is good.
Chesterwood is 122 acres of property in Stockbridge that was the summer home (above), studio and gardens of Daniel Chester French, the sculptor of (among other things) the magnificent Lincoln Memorial in Washington D.C. The workshop/studio is especially interesting to tour, with its huge door and standard gauge flatcar on an indoor railway track that allowed huge pieces of sculpture to be transported.
(Above) Naumkeag, the late 1800’s shingle-style 44-room summer home of the Choate family, is also in Stockbridge. It is especially notable for its 48 acres of incredible and unique gardens: the Afternoon Garden, Tree Peony Terrace, Rose Garden, Evergreen Garden, Chinese Garden, and the Blue Steps fountain.
Stockbridge’s lovely theatre, the Fitzpatrick Main Stage, is housed in a white clapboard building with arched windows, deep green shutters, a wildflower garden and a large porch (for intermission cocktails). We attended the premiere of Terence McNally’s play Frankie and Johnnie at the Claire de Lune. When the theatre lights were completely extinguished, the sounds of enthusiastic lovemaking could be heard…. the lights came up to reveal a Manhattan one-room flat and a sweaty young couple tangled in the sheets. The memory of my brother-in-law’s face still makes me smile: he turned to me and exclaimed “you brought us to PORN?” (Nope.) In 2011, we saw the world premiere of “Edith” there, about Woodrow Wilson’s wife – one of the things we enjoy so much about the Berkshires is that new works are often workshopped and premiered there.
The Norman Rockwell Museum and studio in Stockbridge (above) is an absolute delight. To make it even better, while we were there they were hosting an exhibition of Charles Schultz’ Peanuts drawings.
The Mount (above), author Edith Wharton’s country house in Lenox, was designed by the author herself using British, French, and Italian influences. We enjoyed touring the house and gardens, and taking in a short classical concert on the terrace.

One of our favourite spots for dinner in Lenox is at the Cranwell Resort, which has since been rebranded with its original name, Wyndhurst Manor. Our first visit had been during Christmas season a few years prior, when the Gilded Age mansion was fully decked out in its Christmas finery. Each summer the resort hosts The Capitol Steps, a politically-inspired improv troupe (their motto is “we put the mock in democracy”). With ever-changing targets in U.S. politics, we were happy to take in another performance. Their song parodies are especially hilarious.

Ventford Hall, above, a Gilded Age (in Canada, we’d call it Victorian) home in Lenox, built in Jacobean Revival style, was used in the film adaptation of John Updike’s “The Cider House Rules”. The 50-room mansion was originally built for the sister of J.P.Morgan, and was later owned by Margaret Vanderbilt; the Berkshires was the summer home of many of the 19th and 20th century’s wealthiest New York families. The house had been used as a dormitory and even community housing before falling into disrepair. By 2015, restoration had been ongoing for almost 20 years, but was nowhere near completed.
An absolute highlight of our time in Lenox was attending the world premiere of Mother of the Maid at Shakespeare & Company, ( above – where we had taken in Shakespeare plays in the past, both in the indoor theatre and on the open air stage), with it’s Emmy-award winning writer Jane Anderson in the audience. We had front row seats at stage level, and were first to our feet at the end of the play – along with the rest of a clapping, cheering, crying audience. In 2018, Glenn Close took the starring role of Joan of Arc’s mother when the play was presented off Broadway.
The Guthrie Centre at the old Trinity Church in Great Barrington (above). This is THE church that Alice lived in, and in which Arlo Guthrie and his friends enjoyed a “Thanksgiving dinner that couldn’t be beat”. The area where the pews have been removed is no longer filled with half-a-ton of garbage (thanks to Arlo, his red VW Microbus and his shovels and rakes and implements of destruction) and is now used as a community centre and intimate concert venue. We heard the wonderful Marc Berger there.

Great Barrington is full of colourful century homes, antique shops, brewpubs, and restaurants (where else can you line up outside a Zagat-rated pizzeria behind James Taylor or Arlo Guthrie and have not one single person act like it’s not just a normal day?), as well as lots of scenic walking trails.

On a previous visit we stayed in a suite at Stonegate Mansion (above), a lovely old home that has been converted into a self-catering hotel consisting of 7 apartments; ours had the most beautiful weathered hardwood plank floors so memorable that years after our stay there I used them as an inspiration for new flooring in our house, a ceramic tile-faced fireplace large enough for me to stand in, the original isinglass windows, and 10 foot high cranberry red living room walls – and ceilings – with white plaster beams.

Of the Berkshire towns, to my mind (and I’m open to being convinced otherwise) Pittsfield is the least charming, but it is home to two wonderful arts venues: Barrington Stage Company, where we enjoyed Neil Simon’s “Lost in Yonkers”, and the Colonial Theatre, where we enjoyed watching Kate Baldwin and Jeff Moss in a revival of “Bells Are Ringing”. My favourite performance ever at the Colonial was a couple of years earlier when we saw James Taylor there in a solo concert; the acoustics and atmosphere were both perfect.

My in-laws are not huge art gallery fans, but I am, and Ted humours me, so we also visited the Clark Institute in Williamstown, where in addition to artwork there is a wonderful selection of historic musical instruments…

…, and the Sol Lewitt wall drawing exhibition at Mass MOCA (Massachusetts Museum Of Contemporary Art) in North Adams, before visiting Jack’s Hot Dog Stand: $1.00 boiled hotdogs, or single patty grilled burgers, or fries, served with one of ketchup or mustard, on paper plates at an old-fashioned arborite counter!

After leaving Massachussetts, we headed northeast to Nova Scotia, to visit #2 son and his family on Canadian Forces Base Greenwood in the beautiful Annapolis Valley. En route back to Ontario after our visit, we cut through the northeastern U.S. and got another quick fix of The Berkshires with a stop at the Dr. Seuss National Memorial Sculpture Garden in Springfield, Massachusetts.

I’m ready for another visit any time.

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