Driving out to the Berkshires is one of my favorite summer adventures.  The lush green of the rolling hills, cute small town centers, historic houses and museums, and artistic flare provide something for everyone. 

This year’s visit centered around a concert at Tanglewood. The summer home of the Boston Symphony Orchestra, Tanglewood offers classical concerts throughout the summer; however, they also open up their stage to popular artists as well.  I had been to Tanglewood before – over a decade ago – and I remembered the experience fondly. This time made me fall even more in love with the venue.  While most concerts focus on the stage performance of the musician, Tanglewood is more about the musical ambiance.  While there are typical assigned seats under the Koussevitzky Music Shed where you can enjoy the stage performance, most people – including myself – prefer the laid back atmosphere of the lawn. Because Tanglewood allows people to bring picnics and chairs, it’s fun to get a group of people together to create an afternoon of eating, drinking, and talking before the show begins.  Some people even decorate their set ups with chandeliers and flowers. There are also further flung fields where people play frisbee or spend the afternoon painting the beautiful Berkshire vistas.

Since Tanglewood is more than two hours from Boston, it makes sense to spend a few more days fully immersing yourself in the area – and there is lots to do. 

Also in Lenox is The Mount: Edith Wharton’s former house. Built in 1902 by Edith and her husband Teddy, The Mount’s architecture and landscape design was inspired by a mix of European and American traditions. The estate features a Georgian Revival Stable, formal Italian gardens, woodland trails decorated with art installations and lush fern beds, and the classically inspired Main House. 

While Wharton is best known for her literature, The House of Mirth (1905) and The Age of Innocence (1920), she previously published The Decoration of Houses (1897) with architect Ogden Codman while living among the high society in Newport, Rhode Island. The Mount is in essence a living example of Wharton’s design philosophy.  Just as her book values practicality over showmanship, the estate’s willingness to allow guests to sit on some of the furniture, see Wharton’s writing process first hand, and browse through historic documents, made the place feel less of a showpiece and more of an intimate experience.

Informational panels throughout the two main floors detail Wharton’s personal life, career, and connections.  It also provided some more in depth information about Edith Wharton’s finances and her personal relationship with her husband. Even though I have studied Wharton’s literature in the past, I enjoyed learning more about her internal and external experiences. 

Another influential American artist with ties to the area is Norman Rockwell. Later in his career (1953), he set up his home and studio in neighboring Stockbridge. The Norman Rockwell Museum chronicles his career as an illustrator for The Saturday Evening Post and Look Magazine.  On site is also his studio – preserved as he left it. The museum also allows guests to wander around the 36 acre estate to enjoy impressive views, the Housatonic River, and a few onsite sculptures. 

With leftovers from our Tanglewood picnic, we enjoyed a picnic lunch at Balderdash Cellars in Richmond. Balderdash Cellars is celebrating 15 years of producing small batch wines. While their grapes come from California, there is a small vineyard below the wine house and provides the classic vineyard vista.  I appreciated that the venue provided a variety of seating options and stacked chairs/tables so that guests could choose their perfect spot. 

I found my way back to West Stockbridge to enjoy some of the places I previously visited – Shaker Mill Books, No 6 Depot, Hotchkiss Mobiles Gallery & Studio, Public Market – and finally visit TurnPark Art Space.

The 16 acre sculpture park is set within the forest just outside the center of West Stockbridge.  It’s the type of place that asks you to wander, look closely, and slow down.  Spread around the former marble and limestone quarry are a variety of art installations – both small and large. Some are almost hidden within the environment while others command the open spaces.  Chairs and tables are scattered throughout the park for people to sit and enjoy.  There are also two small indoor exhibit areas – the Gatehouse and Garage gallery. 

Another new adventure for me in West Stockbridge was a visit to the Charles H Baldwin & Sons General Store.  Historically known for their extracts – which they still sell – the funky old time general store is filled with all types of odds and ends. From retro candies and food items to kitschy socks and stickers, it’s fun to browse its wares.

Based mainly on my August 2026 visit.