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.
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.
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.
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.