Summer Weekend in the Berkshires
Spending a weekend of culture and nature in the Massachusetts Berkshires is our longstanding family summer tradition. We keep coming back every summer (with friends and kids who are now teens) and sharing our trips with you. Here is our recent three day-two night trip itinerary so you can follow along for your own Summer in the Berkshires Weekend.
Planning Tips. There is so much to do in the Berkshires for culturally-curious folks – with music, theater, dance, fine arts and historic architecture offerings. The main event of our Berkshires summer weekend is Tanglewood – the beautiful summer home of the Boston Symphony and Boston Pops; so we try to fit several concerts into our tight agenda and there are way more musical choices offered in Tanglewood than there is time in any weekend. (Check out our recent story on spending an entire weekend enjoying the many Tanglewood offerings).
Friday
We took half day off and started the drive around noon from a Boston suburb. We traditionally start our Berkshires weekend with a lunch and drinks on the porch of Red Lion Inn in Stockbridge – America’s oldest running inn. It’s not about the food so much as gathering together to toast the beginning of another epic Berkshires weekend. Afterward, you can stroll Stockbridge’s Main Street for iconic Berkshires views straight from the famous Norman Rockwell painting (which is housed in the nearby Norman Rockwell Museum) – before checking into your hotel (see lodging section below).
This evening we headed to an outdoor performance of The Twelfth Night (directed by Kaye Lohler Amory) at Shakespeare & Company (Be sure to check out the calendar for your weekend and mention the kids/teens for special pricing). This is a very special multi-stage (indoor/outdoor) theater, that functions as a center for theatrical training and community education rooted in Shakespearean ideas. (You could also do a backstage tour of this theater).
But tonight was the Twelfth Night- all about the playful chaos, engaging with the theatrical community and the outdoors. (The following day we came back for a more intimate Fireflies on a small stage of their Elayne P. Bernstein Theater).
Saturday
We started the day with a walk at The Mount, writer Edith Wharton’s estate in Lenox. (They often close early on summer Saturday afternoons for weddings). If it is your first visit, I recommend touring the inside of the beautifully preserved house. We have already visited many times with the tour, so today we are just admiring the (annually updated) sculptures on the Sculpture Walk and taking in the iconic gardens.
It was raining heavily by the time we finished lunch in Lenox (it’s Asian fusion for us this time at Yao Asian Fusion) – and we got notifications that our outdoor concert at the Jacob’s Pillow Dance Festival (in Beckett) has been cancelled. This is the country’s oldest dance festival with the world’s leading dance companies performing on the outdoor and indoor stages every summer. We have traditionally frequented their summer school’s contemporary dance outdoor concerts but these are weather dependent. (Our day was frankly a bit overbooked so we took the opportunity to spend time at our resort hotel and watch the third place FIFA World Cup match and regroup before our evening event.)
At 2 pm the adults in our group headed to the (small stage) performance of the intimate Fireflies at the Shakespeare & Company. This theatrical experience was all about human connection and its twists and turns as we grow older. The company has another very “human” play – Frankie and Johnny coming up July 30-August 23. I already miss our summer theater experiences and am thinking about coming back in the fall. (They have fall and some limited winter programming).
In the evening we have our “Main Event”: the Tanglewood. There are concerts almost every day during the Tanglewood summer season –with Boston POPS and other popular artists’ performances in a variety of musical styles complimenting Boston Symphony’s traditional classical programming (check out my Tanglewood season overview in this post). It was a rainy night so we were inside the historic Koussevitzky Shed (instead of our usual lawn; Shed tickets start at $26). Evening (8pm) concert tickets include access to the the 6 pm Prelude Concerts (Tanglewood in itself really is an-all weekend affair!)
This Saturday we were privileged to hear the Japanese composer Joe Hisaishi conducting his own pieces from the popular Japanese cinematic sound tracks (with Meredith Wohlgemuth, distinguished American soprano). Also in the program is French pianist Jean-Yves Thibaudet performing Ravel’s Piano Concerto. You can always count on the extraordinary depth of multicultural talent at Tanglewood. It’s like the Olympics of the music world, with every performer representing the pinnacle of their genre. When you see an artist on the program, you know you are in for something exceptional.
I caught myself teary-eyed at the sound of the final orchestra encore of Merry-Go-Round from “Howl’s Moving Castle” soundtrack. There were Hisaishi fans from all over the country at the concert tonight.
Sunday
We start Sunday having coffee and sweets at the Chocolate Springs in Lenox. There was a Family Concert this morning at Tanglewood, but we are freeing some energy for the afternoon concert (and our teens are a bit older than the target audience for family concerts).
Sunday afternoon Boston Symphony concerts are the core events of the Tanglewood summer (through August 23 this summer of 2026; Popular artist series are happening through September 6). On Sunday July 19th Andris Nelsons was conducting Haydn Symphony No. 22 (The Philosopher), Shostakovich’s Piano Concerto (Daniil Trifonov, piano, Thomas Rolphs, trumpet) and Beethoven’s Symphony No. 2.
We came early, set up for the picnic, walk the beautiful grounds and breathe Berkshire mountainous air.
We reached the Ozawa Hall when the morning Chamber Music Concert was playing the encore (by the TMC Fellows). There is always so much happening in Tanglewood (and summer tickets prices start at $26; kids under 18 enter for free at the lawn).
Musicians and some audience members were wearing red ribbons in support of the beloved Boston Symphony Conductor Andris Nelsons whose contract expires after Tanglewood summer 2027.
Before our drive home from the Berkshires we like to stop for coffee good-byes on the terrace of the historic Red Lion Inn on Main in Stockbridge. It has been a full circle weekend and we are already planning a comeback!
Where to Stay. Summer accommodations in the Berkshires get expensive. Our recent stay at Holiday Inn Club Vacations Resort in Lee offered some of the most reasonably priced apartment style accommodations in the Berkshires with full resort amenities (and mountain views). We shared a two-bedroom two bathroom unit with a fully equipped kitchen with another small family. In years prior we also stayed at Yankee Inn and Hilton Garden Inn in Lenox.
