By Victoria@celebratetheweekend
In Adult Birthday
Jun 28th, 2015

June is a big birthday month in my family as both my mom and my daughter celebrate their days (You can read about where to take your kid on their birthday in Boston here).   For me there is no better birthday celebration than spending the day with those I love doing things that I enjoy the most  – and that, of course, is travelling.  I also love planning trips for my family.  So for my mom’s big birthday a couple of years ago, my dad and I organized a DAY WITH THE ARTS day trip to the Berkshires – for 30 friends and family.  I am no stranger to planning an extended family group travel, but a trip for 30 was a first for me.

The guests received their invitation with all the details of the 14-hour celebration in advance, but we kept it a surprise from a birthday girl until the morning of the trip (we did tell her that she would not have to worry about a thing!).

The Berkshires is a naturally beautiful mountainous region in Western Massachusetts that is also a home to world class cultural institutions and summer music, dance and theater festivals.  It is a 2-3 hour drive west of Boston (depending on the specific destination and traffic).

A day trip to the Berkshires, MA for 30 friends and family

We hired a bus (and a driver) from Local Motion of Boston and also separately engaged a private tour guide. After quick champagne breakfast at home (bus driver not included), everyone boarded the bus and the journey began.  I know, champagne breakfast and quick do not really sound good in one sentence, but we had a big day ahead of us. It was a 3-hour drive from my parents’ house South of Boston to our first destination in Williamstown.

To keep everyone entertained, we played How Well Do You Know a Birthday Girl Trivia and listened to our travel guide’s stories about Berkshires’ history and arts.  (Travel mishaps happen, and we missed our planned nature stop of Shelburne Flower Bridge.)

We did stop at the The Clark Art Museum in Williamstown.

A day trip to the Berkshires, MA for 30 friends and family

The collection of the Clark Art Institute is especially 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. (Admission is $20, free for children under $18; Clark hosts various family events through the year, such as Van Gogh and Nature Family Day on July 26th or Free Fun Friday on August 28.)

Clark has not only a world class impressionist collection but also impressive grounds, so everyone set to explore on their own.  Birthday girl had lots of company to choose from- a built-in benefit of the birthday trip with friends!


A day trip to the Berkshires, MA for 30 friends and family

Beautiful grounds of the Clark Museum in Williamstown, MA

After a picnic of catered sandwiches we brought from home for everyone, we re-boarded the bus to our next Berkshires destination in Stockbridge, 45 minutes away.

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.  On this trip we headed to Chesterwood, the country home, studio and gardens of Daniel Chester French, sculptor of Abraham Lincoln for the Lincoln Memorial in Washington, DC.

A day trip to the Berkshires, MA for 30 friends and family

Chesterwood, Lenox

Chesterwood is a recognized National and Massachusetts Historic Landmark situated on 122 acres of beautifully landscaped gardens.  French (1850-1931) lived and worked on the estate 6 months a year.  Many of the plaster sketches (including models of Abraham Lincoln for the Lincoln Memorial), are on view in the Studio.

A day trip to the Berkshires, MA for 30 friends and family

Mom is happy. Trip was a success!

Since our visit, the house has undergone a renovation and you can now visit a newly rehabilitated studio, as well as tour the nine-bedroom residence, and explore the formal and wooded walks throughout the 122-acre estate.  Some of the formal gardens were created by the sculptor himself.

A day trip to the Berkshires, MA for 30 friends and family

Here is our group exploring the grounds with a tour guide provided by the Museum (another benefit of the group travel!)

A day trip to the Berkshires, MA for 30 friends and family

A day trip to the Berkshires, MA for 30 friends and family


We then had dinner at a small French restaurant off  Main Street in Stockbridge which became our private dining room for the special evening.

A day trip to the Berkshires, MA for 30 friends and family

The drive back to Boston was shorter (2 hours) and everyone serenaded the birthday girl, accompanied  by a beautiful guitar playing  (courtesy of my dear husband, who is also behind all the pictures on the blog).

It was a day trip to remember, and quite possibly the longest continuous birthday party ever!

A day trip to the Berkshires, MA for 30 friends and family

Project “Birthday Day Trip” organizers with the Birthday Girl



  1. Anna Burdman says:

    My dear daughter, thanks again for all the happy moments I had that Day and as I was reading this post! I feel like I am a Queen-Mother again… You are a great fun organizer, especially for those you love!
    With love, your Mom.

  2. AKASH GOLA says:

    Hi Victoria,
    Personally speaking, you write very well.
    I am fan of your blog, you always write very informative articles.
    Thanks for sharing again.

  3. Anda says:

    What a beautiful celebration, Victoria. It’s so good to have a big family and organize get-togethers like this. I would have liked to be invited to such a fun party and beautiful destination.

  4. Victoria@celebratetheweekend says:

    Thank you for your kind words, Anda. I have a feeling you would be a fun person to have around at our trips:)

  5. Ruth says:

    From your photos, I can see you guys had a wonderful day. I have to congratulate you for planning something like this. 30 people? I do not think I can do it.

  6. What a wonderful idea, and what fantastic memories for the birthday girl and everyone who participated! It looks like everyone had a fantastic day and enjoyed the Berkshires very much. It IS a great place to visit and celebrate!

  7. Rhonda Albom says:

    Sounds like a wonderful celebration. You are lucky to have family that can do this, mine is scattered all around the world.

  8. Connie Reed says:

    What an awesome birthday celebration! It’s a LOT to plan but definitely worth the effort.

    • Victoria@celebratetheweekend says:

      Thank you, Connie! I remember the entire experience fondly, except may be the missing stop part but the company gave us a sizable discount for the mistake. And- I should have paid attention instead of having too much fun leading the Trivia with the group:)

  9. Lisa Woood says:

    oh wow what a fabulous birthday celebration, and its all organised! Love it 🙂
    Happy Belated Birthday for your Mum and Daughter.
    Fantastic organizing so many people for one occasion 🙂

  10. […] birthday celebration trip to the Berkshires Victoria organized for her mom and 30 guests (“A Day with the Arts in the Berkshires. Birthday Trip for 30 Friends and Family“) , or the list of places her family visited in San Francisco (“Our Family’s Top […]

  11. Aidan A-lehh says:

    Very well written article, thanks for the information and keep writing such amazing articles.
    I am great fan of your blog, thanks.

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