Things to Do in the Berkshires of Western Massachusetts in the summer

Weekend in the Berkshires: 2-day itinerary (with or without the kids)

Summer 2020 update: Many museums have reopened with social distance protocols in place. Check individual websites for details. Tanglewood Music Festival and Jacob’s Pillow dance festival are not happening (although Tanglewood grounds are open for visits with prior reservations); Shakespeare and Company’s summer theater season is not running.

The Berkshires  region in Western Massachusetts offers access to world class cultural attractions set amidst the gorgeous natural surroundings. My favorite time to visit is summer when renown music, dance and theater festivals, and the Berkshire’s famous historical houses offer majority of their programming, with many events happening in the beautiful outdoors.

Here is a 2-day sample Berkshires itinerary based on our weekend trip in a couple of summers ago.

You may also want to check out the “visuals” in our youtube video:

We live a little over 2-hour drive away and try to visit several times each summer (so I also provided some alternatives which we have experienced on other trips).

Where to Stay. Lenox, Lee or Stockbridge are most central areas to stay with the attractions in these towns being only several miles away from each other;  another “center” of attractions is Williamstown, which is a 30 minutes drive from Lenox. Berkshires’ accommodations in the summer could be expensive, but mid-week rates are often discounted, and you may also want to consider staying a bit less central, like Pittsfield, which is a 25-minute drive from Lenox. During this visit we stayed in Seven Hills Inn (next to the Mount) in Lenox.

Things to Do in the Berkshires of Western Massachusetts in the summer
Our view from the breakfast terrace at Seven Hills Inn

Day 1.

Start the day with a visit to one of the area’s art museums. On this trip, we visited Frelinghuysen Morris House Museum – former home and studio of American abstract artists George L.K. Morris and Suzy Frelinghuysen, set on a 46-acre estate in Lenox. Museum houses the couple’s paintings, frescoes, and sculpture, as well as a collection of American and European Cubist Art.

Things to Do in the Berkshires of Western Massachusetts in the summer
Modernist “block” house features original furniture and design

A 10-minute woodland walk from the parking area took us to the House. (A golf cart shuttle is available for those needing assistance.)

Things to Do in the Berkshires of Western Massachusetts in the summer


Things to Do in the Berkshires of Western Massachusetts in the summer
The Garden

We joined the 10am guided tour and learned not only about the life and work of this fascinating American couple and their art, but an abstract art principals based on the paintings and design objects throughout the house. Tours are included with admission and are offered hourly Thursday-Sunday, June through October; call ahead for details 413-637-0166. There was another family with kids on the tour with us, and I think the tour is a wonderful educational opportunity for tween and teens interested in art.

(Our other favorite art museums in the Berkshires (both with beautiful grounds) are Norman Rockwell Museum in Lenox and The Clark Art Museum in Williamston. Clark‘s collection is rich in French Impressionist and Academic paintings, British oil sketches, drawings, and silver, and the work of American artists Winslow Homer, George Inness, and John Singer Sargent.)

For lunch, choose one of the many eateries along the main streets of Lee, Lenox or Stockbridge.

In the afternoon, head to Shakespeare & Company in Lenox for a superb theater performance. This is not an ordinary theater, but a center for theatrical training and community education rooted in Shakespearean ideas (with modern twists, of course). (Here is our backstage tour of this theater)

On our weekend trip that summer we saw “Unexpected Man” by award-winning French playwright Yasmina Reza (directed by Seth Gordon) with Corinna May and John Woodson (check this calendar for summer 2019 performances and dates.)  The play first premiered in London in 1995 and has been since staged throughout the world.  I didn’t expect my teen to respond  so well to the play about two middle-aged people sitting in a train compartment together but alone in their thoughts, but he loved it! My son’s true theatrical love is Shakespeare and I hope to return to “Shakespeare & Company” to watch a Shakespeare’s play.

The summer’s programming also includes a family-friendly Shakespeare on the lawn of the Mount (Edith Wharton’s home in Lenox) with the grounds open for picnicking prior to each performance. In 2019 it is the “Taming of the Shrew“.  (Tickets could be purchased online or call (413) 637-3353; be sure to inquire about senior and student discounts.)

“Shakespeare & Company” has the most beautiful theater grounds I have ever encountered, with several stages (including summer Elizabethan’s performance tent) sharing the property.

Things to Do in the Berkshires of Western Massachusetts in the summer
The Shakespeare’s Garden on the grounds of Shakespeare & Company

Another great place to spend a summer afternoon is Jacobs Pillow Dance Festival in nearby Beckett. This is America’s longest-running international dance festival which brings together world’s leading dance companies to the Berkshires every summer. Take advantage of the free family-friendly Inside/Out outdoor performances  on Wednesdays-Saturdays during the annual summer dance Festival.

Things to Do in the Berkshires of Western Massachusetts in the summer
Jacobs Pillow’s festival outdoor performance

Day 2.

Start your day 2 with a visit to one of the area’s beautifully preserved house and gardens, such as The Mount, Edith Wharton’s estate (open daily from May to October, kids visit free). This National Historic Landmark features three acres of beautiful formal gardens designed by the author herself.  It is also a  cultural center devoted to preserving the legacy of Wharton’s work (Wharton was the first woman Pulitzer Prize winner for Fiction  for her novel “Age of Innocence” . The Mount hosts a variety of musical, literary and theater events and exhibits throughout the year (update for 2019: “Shakespeare & Company’s” “Taming of the Shrew” is performing through August 17 on Mount’s lawn).

Things to Do in the Berkshires of Western Massachusetts in the summer
Modern Sculpture Exhibit currently on display at the Mount.

The classical revival house, based on the principals outlined in Wharton’s book, “Decoration of Houses” was built in 1902, and served as the inspiration for some of her best work, including “House of Mirth” and “Ethan Frome”.

Things to Do in the Berkshires of Western Massachusetts in the summer

Ms. Wharton was as proud of her gardens as her literary achievements (if not more!) and you can see why.

Things to Do in the Berkshires of Western Massachusetts in the summer


Things to Do in the Berkshires of Western Massachusetts in the summer
This is  me, feeling at home in the Berkshires (in the Gardens of the Edith Wharton Estate)

House, Garden, Backstairs, and Literary Tours guide-led (or self) tours are included with admission. Ghost Tours (recommended for children 12+) require advance reservations. Long term goal of the restoration project is to offer free public access to the grounds.

(Terrace café serves up the best view of the Berkshires (along with some light lunch).

On this trip we also visited Naumkeag house and garden (open Memorial Day weekend to Columbus Day daily, 10-5; there are daily tours of house and garden) but I recommend choosing one house and garden for a day and explore another glorious property on another weekend trip (or a stay an extra day if you can!).

A national Historic Landmark, Naumkeag is an architectural masterpiece of the Gilded Age (built in 1885);  it is a family summer home of the leading 19-century attorney Joseph Choate. Nothing had to be recreated inside the house, as it was never lost. (It was bequeathed in its entirety with original furniture and artwork, including a portrait by John Sargent) so visitors can experience the house as guests of the family once did.

Things to Do in the Berkshires of Western Massachusetts in the summer
Naumkeag Estate

Naumkeag features one of America’s first modernist landscapes, created by Mable Choate who spent 30 years developing 8-acres sequence of “garden rooms”.

Things to Do in the Berkshires of Western Massachusetts in the summer
Afternoon Garden


Things to Do in the Berkshires of Western Massachusetts in the summer
Panoramic views of the Monument Mountain from the lawn.


Things to Do in the Berkshires of Western Massachusetts in the summer
Famous Oak lawn where the Choate family picnicked prior to purchasing the 49-acres estate in 1884.

(On other trips, we have also visited and loved Chesterwood in Stockbridge, a country home, studio and gardens of Daniel Chester French, sculptor of Abraham Lincoln for the Lincoln Memorial in Washington, DC. (see my trip report here).

In the afternoon, we headed for a 2:30pm performance in Tanglewood, summer home of Boston Symphony Orchestra (celebrating its 75th season this summer with diverse programming of classical, jazz, popular artists and film musical events; more information HERE).

Sunday afternoon performances are my favorite for a visit with a family (Here is my post about visiting Tanglewood with kids). For a more romantic (literally) “candlelight” setting choose Saturday evening concert. We made sure to arrive by 1pm for the 2:30 performance to pick the best picnic spot under a tree and take advantage of the kids’ programming. There are special pre-show programs for children, including Kids’ Corner and Watch and Play, and an annual Family Concert.

Things to Do in the Berkshires of Western Massachusetts in the summer

Things to Do in the Berkshires of Western Massachusetts in the summer

Before your drive home from the Berkshires make sure to have a “slightly overpriced” coffee experience on the terrace of the historical Red Lion Inn on Stockbridge’s Main Inn to people watch and soak in the events of the day. You may remember Stockbridge’s Main Street (with historical storefronts and the Red Lion Inn) from famous Norman Rockwell’s painting which is housed in the nearby Norman Rockwell Museum.

Things to Do in the Berkshires of Western Massachusetts in the summer

Note on Planning. I suggest visiting no more than 2 places/events in a day, diversifying your daily choices and making sure (weather permitting) to spend a large portion of the day outdoors.

Note on Food. There are some great restaurants in the area, but we are usually so busy packing events into our Berkshire weekends and so in love with its outdoors that we do a lot of picnics.

Getting There. Lenox, Massachusetts, which is approximately 2.5 hour drive from Boston and New York City.

Other Family-Friendly Suggestions for Your Visit:

Hancock Shaker’s Village in Pittsfield (former utopian religious community and now an outdoor history museum

Animation Museum

Berkshires Botanical Gardens in Stockbridge offers rich educational programming make visit family-friendly

Ramblewild tree top adventure park

Berkshires Museum (art, nature and history)

Mass Moca Museum of Contemporary Art


16 thoughts on “Weekend in the Berkshires: 2-day itinerary (with or without the kids)”

  1. Looks like a great weekend. I have friends that often go to the Berkshires and I didn’t even understand where it was or what the draw was. Now I see. Lovely post!

    1. Victoria@celebratetheweekend

      Thanks, Karilyn! I did not understand what it was all about until I went myself…and then I was hooked!

  2. Very beautiful place. I’d like to visit, but then the world is so big… where should I start. It seems that you were really lucky with the weather. I’d imagine a sunny day is essential to a place like the Berkshires. The summer dance festival looks fun too.

    1. Victoria@celebratetheweekend

      It’s the mountains’ region so weather changes several times a day. it rained throughout the day when we were there, yet we managed to sit outside through the concert without a drop!

  3. What a great collection of tips on what to do in the Berkshires. I wish I knew about the “Hamlet”! That’s my favorite Shakespeare play and I like to see how differently different actors and directors spin it. It sounds like you had a great two-day trip. I love the photos!

    1. Victoria@celebratetheweekend

      Thank you, Jolanta! I am sorry I missed Hamlet too- it sounded like a great open air performance for the entire family. I plan to come back to Shakespeare and Co next summer for sure!

  4. Pingback: 2015 Year in Pictures of weekend celebrations

  5. Pingback: Attending Tanglewood performance with kids

  6. Pingback: Weekend in Massachusetts Berkshires with Kids

  7. Pingback: My “anti-yoga” Retreat at Kripalu | WEEKEND CELEBRATIONS WITH VICTORIA

  8. Pingback: Summer Weekend Trips from Boston

Leave a Comment

Your email address will not be published. Required fields are marked *