24-hour escape to the Berkshires

24-Hour Couple’s Getaway to the Berkshires

We spend a family summer weekend in the Massachusetts Berkshires every year but we haven’t had a chance for a couple’s romantic weekend in the Berkshires weekend in a long time.  So we aimed to make the very best of our 24 hours in Lenox last weekend! Here is how it all unraveled.



24-hour escape to the Berkshires
Tanglewood is the place to be in the summer- for couples and families

We left Boston at 4 pm on a Friday afternoon and headed straight to Tanglewood Music Center in Lenox (it’s a 2-3 hour drive depending on traffic).  For me, Massachusetts summer is just not the same without a visit to Tanglewood, summer home of Boston Symphony and Boston Pops orchestras with a rich multi-genre programming.  To experience Tanglewood with a family- day time concerts are best (and summer Sundays have enhanced family pre-concert offerings- read all about it here), but for a couple’s date night- I recommend (Friday or Saturday) evening performances.  Other parents seem to agree with me as there were barely any kids attending the evening performance last Friday.   (it got chilly at the second part so be sure to come with a sweater).

24-hour couple's escape to the Berkshires
Tanglewood summer

We had the lawn tickets (courtesy of the Boston Symphony Orchestra) and a picnic was a big part of our evening.

Our visit coincided with Opening Night  in Tanglewood with Conductor Andris Nelson leading Boston Symphony to perfection in their performance of Mozart and Tchaikovsky.  World famous pianist Lang Lang’s Encore of Chopin’s Nocturnal was simply mesmerizing.  Here is a line-up of Tanglewood performances for the rest of the summer.

THE ART OF LOUNGING (in historic inns)

With theater show in the afternoon, I wanted our Saturday morning to be all about relaxation, coffee and lounging (not necessarily in that order).  I did not really plan a historic inn hopping that followed, but my quest for perfection in relaxation (and coffee) often brings me to amazing places.

Cranwell Resort, Lenox

We started our mini-journey at the Cranwell Resort in Lenox.  We admired its hilltop Tudor-style century old centerpiece mansion and the views of the Berkshires. We later learned that Reverend Beecher (brother of Uncle Tom’s Cabin author Harriet Beecher Stowe) who himself was active in the women’s suffrage and the anti-slavery movements and at some point even had presidential aspirations, was one of the original owners of the property.

There is a golf course (which turns into a cross-country ski trail in the winter) and a famous spa (one of the largest in the Northeast).   Despite the beauty of the property, we could still see route 20 in the distance from the restaurant terrace and decided to continue our search for complete and utterly relaxation.

Which brought us to…the center of Main street Stockbridge, and our old favorite, Red Lion Inn.

24-hour escape to the Berkshires
Red Lion Inn, Stockbridge

It is located on the relatively busy street in the center of Stockbridge (straight from the Norman Rockwell painting), but we have been enjoying our coffees on its terrace for years (and not just us- the Inn has hosted five U.S. presidents, including both Roosevelts).  Built in 1773, it is the oldest inn in the country in the continuous operation.  Originally just a rest stop for the carriages traveling between Albany and Boston, it is now a revered place to sleep and eat in the Berkshires (or to have coffee and people-watch on the porch).  Unfortunately for us, the coffee service on the porch starts after noon, so we had to move on.

It was now time for lunch and we stumbled upon the name Blantyre in the brochure – which seemed to work with the theme of the morning – so there we went!

24-hour escape to the Berkshires
Newly renovated Blantyre

This Gilded Age mansion (1901) has been “recently refurbished for a new age of Gilded Grandeur”, said the brochure.  And we knew that it was true the moment we entered its welcoming beautifully decorated new-old common rooms.

Just outside the lobby area – on the porch overlooking the Berkshire hills, we knew that we found what we were looking for all morning and stayed for lunch and coffee. And then some hammock lounging.

24-hour escape to the Berkshires
Blantyre, Lenox
Relaxing at the Blantyre



Shakespeare and Company Theater, Lenox

We are partial to the magic of the Shakespeare and Co, a multi-functional theater complex we have toured (backstage) last summer.   This time we were invited to for Morning after Grace (in production through July 15) on the intimate Elayne P. Bernstein stage (featuring Corinna May, Kevin Vavasseur and Steven Barkhimer).  It is a farce of second changes, a play- according to its director Regge Life- about “real things and real people”.   There are only three characters in it and you quickly feel at home -and happy to spend the next two hours with.   It was not “all roses”, but we left the theater feeling light and with a desire to be back.

The Company’s mission is built on “exploring the universal themes of human experience”  – in Shakespeare’s and modern plays alike.

Contemporary plays Creditors by August Strindberg (July 19-August 12) and Mothers and Sons (August16-September 9) by Terrence McNally move in later in the season;  and there is of course always Shakespearean presence.  This year it is Macbeth (July 3-August 5) and Love’s Labor’s Lost which we plan to come to see with the kids.  It is a family-friendly staging of the classic performed at the Mount Estate of writer Edith Wharton (where the house and garden are a treat of their own). Here is a calender for the rest of the summer.

The Mount will host the outdoor family-friendly production of Love’s Labor Lost this summer

For more ideas on how to spend 24 (or a 100!) hours in the Berkshires, check out our ideas from  With or Without the Kids itinerary.  For things to do during the Kids’ Weekend In the Berkshires, read this post.

Where we stayed.  Finding reasonably-priced lodging to experience all this goodness in the summer is not an easy task in the Berkshires.  This time we have used our HH points at the newish Hampton Inn in Lenox and were pleasantly surprised by the size of the rooms.  Check out this review of another property we stayed in in one of our visits- Seven Hill Inn located right next to the Mount.

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24 hour date in the Berkshires of Western Massachusetts



6 thoughts on “24-Hour Couple’s Getaway to the Berkshires”

  1. Wow you saw a lot in 24 hours! Glad you fit in a little time for lounging! It looks like such a charming area and the music and theatre sound wonderful.

  2. From what you are describing Tanglewood is kind of like the Hollywood Bowl here, in California. It’s beautiful to listed to some classical music under the stars in summer, so no wonder you had fun. The rest of your visit was fun too, so good for you that you took off for a week-end. #TheWeeklyPostcard

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