Stockbridge and Great Barrington

Readers, I proudly present to you a first in Catherine the Greatest history-- a guest blog post! Many loyal readers have sent me subtle inquiries about a mysterious Josh figure who has been mentioned in several recent posts. He is a leading expert in small-town America, and exhibits a passion like none I have ever seen for the charming and quaint. What better way to debut him to my public than with a mandatory writing assignment! Without further ado, I bring you...

 Wandering the West
by Josh
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For most of us living in the Metrowest area, western Mass is anything past Worcester, but did you ever wonder what neat places exist in the great West of the Bay State?  For Catherine’s birthday, we took a trip to the southern Berkshires.  We were excited to celebrate and learn more about our great state.

Our trip started by visiting historic downtown Stockbridge which is famed for being the quintessential New England town.  I am undoubtedly a huge fan of small towns, and Stockbridge was no exception.  It has a wonderful blend of small stores to browse, bakeries, eateries, and cafes.  What delighted me the most was the balance between upscale atmosphere and classic New England charm.  Also, this town was also home to Alice’s Restaurant, the basis of the famed Arlo Guthrie song.  The restaurant is now named The Stockbridge Cafe.

After exploring downtown, we headed to a historic home and garden called Naumkeag, a property owned and managed by  The Trustees of Reservations for the enjoyment of the public.  The house served as a country “cottage” for the prominent Choate family.  This cottage is truly an impressive mansion.  The most dazzling part of the property is the gardens.  Much of the garden was designed as outdoor rooms by renowned landscape architect Fletcher Steele.  Miss Mabel Choate, who inherited the property from her family, took a strong personal interest in Naumkeag’s landscape and Fletcher Steele's expertise, working on a multitude of projects for 30 years.  The must-see garden element is the Blue Steps, which consists of a series of fountains flanked by stairs beneath a White Birch grove.

                                                      (the author, posing in front of the famed steps)


After our step back in time to the Gilded Age, we headed to the Norman Rockwell Museum.  I have always been a big fan of Norman’s Rockwell’s art.  I am constantly inspired by his ability to portray everyday life in a way that people of any age and background can relate to. So many of his works bring a smile.  They also bring home the idea of everyday heroes and a sense of community.  Although I had seen many of his paintings in books or online, I was excited to see some originals. I was amazed with how large and detailed most of his paintings were, which afforded me even more respect for my favorite artist.  I have to admit, I was holding back some tears when we viewed the Four Freedoms- this is worth the visit.


For Catherine’s birthday dinner, we visited Great Barrington.  After taking a driving tour we stopped at The Point Restaurant at Thornewood Inn.  One thing we learned about the southern Berkshires was that large hotel and restaurant chains do not exist; instead there are many Inns and unique local eateries. The Point was no exception.  After admiring the beautiful Inn, we sat down for an unbelievable meal.  During a heartwarming conversation with the owner, he talked us into a homemade chocolate ganache cake, that I am tempted to say might be worth the two-hour trip from Walpole to have again.