This site is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as CreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.

On a typical Summer weekend, the chances of you running into a New Yorker in the Berkshires for the weekend is pretty high. Jim “The Travel Organizer,” who last wrote about Portland, Oregon, The Road to Hana, Maui’s “upcountry“, Hong Kong, Austin, San Antonio, Valley of Moon, California, Dubrovnik, Croatia, Split, Croatia, Krk, Croatia, Koper, Slovenia, Mendocino County, California, Auckland, Oslo, the small German town of Speyer and Deidesheim, Oahu, Napa Valley, Venice, Singapore, Bangkok, Sonoma County and Myrtle Beach, and here are his tips should you decide to visit The Berkshires. If you would like to write about your recent travel experiences on The Flight Deal, submit your pitch here. ===

What/where are “The Berkshires”?

Geographically and geologically speaking, the Berkshires are a continuation in western Massachusetts and Connecticut of the Green Mountains of Vermont. It’s hard to believe that these mountains which, for the most part, are little more than rolling hills today were once almost as high as the Himalayas! Culturally, the Berkshires have been a haven for progressive thought; the first successful lawsuit brought by a slave for her (!) freedom took place in Sheffield, MA in 1781 and the founders of the Women’s Rights movement and the NAACP were born in Adams and Great Barrington, MA respectively – all in the Berkshires.

Where we stayed

Honestly, I didn’t spend a lot of time researching lodging options. When my mother-in-law died, my father-in-law “gifted” us the timeshare they had purchased in the Poconos. Love ‘em or hate ‘em, timeshares are “the gift that keeps on giving” (or is it taking?) but I’ve worked hard at extracting value from it and when the Berkshire Mountain Lodge in Pittsfield, MA became available for an exchange of only 5 points – which exactly matched 5 orphaned and expiring points from previous exchanges – I hopped on it with both feet. I booked a week in late spring for an exchange fee of just $179 (I’m considering the annual maintenance fee a “sunk cost” in my calculations). This property has an excellent location, central to everything we wanted to do. It has a very nice indoor pool, a small exercise room, movies to play on the in-room DVD players and free popcorn starting every day at 3pm. All the units are 1-bedroom suites with full kitchens. The Berkshire Mountain Lodge certainly isn’t aspirational but it met our needs perfectly.

What we did

The Berkshires are highly seasonal. We went the week before Memorial Day and many attractions were just opening or beginning to extend their hours. We decided to focus our time and energy on the important influence this area has had on American history, art and literature.

Naumkeag (Stockbridge, MA)

Naumkeag, “a quintessential country estate of the bygone Gilded Age,” is a 44 room “cottage” surrounded by 8 acres of stunning gardens and 40 additional acres of fields and woodland in Stockbridge, MA. Built by prominent 19^th century attorney and, later, U.S. Ambassador to the United Kingdom, Joseph Hodges Choate, Naumkeag, meaning “fishing place”, is the Native American name for the area around Salem, Massachusetts, Choate’s childhood home. We were fortunate to visit on “Home Sweet Home” day, the annual open house at 8 historic properties from Boston to the Berkshires. The “Blue Steps” on the property, designed by Fletcher Steele (regarded as America’s first modern landscape architect) for Choate’s daughter, are one of the most photographed garden features in the U.S. Admission, which includes a complimentary garden or house tour, is $20/adult, $15 for seniors and students 15+, $5 for students 6-14, children under 6 are free.

Hancock Shaker Village (Pittsfield, MA)

The United Society of Believers in Christ’s Second Appearing is a Protestant sect founded in England in the mid-18^th century. Ecstatic dancing during worship, thought to be a means of shaking off sin, resulted in the derogatory label “shaking Quakers” or, simply, “shakers.” The name stuck. The Shakers’ aim was to establish a working heaven on earth which they understood to include the “3 C’s”: celibacy, communal living and confession of their sins. They numbered about 5,000 at their peak, living mostly in New England and New York. Just 2 Shakers remain alive today. Hancock Shaker Village “…brings the Shaker story to life” through its lovingly restored buildings, working farm, exhibits and tours. Tips: (1) Plan to arrive when the village opens and organize your day around the free scheduled talks and programs. I can’t emphasize enough how much this added to our experience. (2) Consult the events calendar when planning your trip; there’s always something interesting and unique happening at Hancock Shaker Village.

Berkshire Museum (Pittsfield, MA)

The Berkshire Museum on South Street (Route 20) in the heart of downtown Pittsfield, MA is an eclectic collection of exhibits spanning the fields of art, science and history (ASH). We were fortunate to visit while “Leonardo da Vinci: Machines in Motion,” featuring 40 working models painstakingly built using tools, techniques, and materials available to the Renaissance genius was on exhibit. Permanent exhibits in the realm of science include “Animals of the World in Miniature”, the very hands-on “Curiosity Incubator” and even a small aquarium. History exhibits include a fur body suit and sled from the first successful expedition to the North Pole, the writing desk of Nathaniel Hawthorne, an Egyptian mummy, Babylonian cuneiform tablet fragments, etc. The museum’s focus on art is, perhaps, the most controversial. In 2018, it sold works by Albert Bierstadt (known for his landscapes of the American west), Norman Rockwell (which had been donated by the artist himself), Alexander Calder and others to secure its future; I hope the juice proves to be worth the squeeze. Tip: There is no parking lot but there is free parking for two (2) hours on Wendell Avenue, one block east of the museum entrance.

Edith Wharton’s estate, “The Mount” (Lenox, MA)

Birding anyone? The Massachusetts Audubon Society offers free birding walks every Tuesday morning from 8-10am which depart from the parking lot for Edith Wharton’s estate called “The Mount” in Lenox. MA. Having never done birding before, I had no idea what to expect but we did get to see our first Baltimore oriole. No binoculars? No problem; Mass Audubon brings a supply to lend. Pre-registration is required as space is limited to 20 to ensure the best experience possible.

Norman Rockwell Museum (Stockbridge, MA)

Everyone knows the name Norman Rockwell from his iconic Saturday Evening Post covers. The artist and his work, much like Charles Schulz of “Peanuts” fame, speak to the human soul of universal values like dignity, innocence and small town Americana. Rockwell received the Presidential Medal of Freedom, our nation’s highest civilian honor, in 1977, 22 months before his death. His Stockbridge studio, left exactly as it appeared when Rockwell died, was cut in two and moved to the museum’s grounds in 1986. Two especially poignant exhibits leave a lasting impression: (1) the “Four Freedoms” room which display Rockwell’s depictions of the freedoms of speech and worship and the freedoms from want and fear President Franklin D. Roosevelt articulated as the principles for which the Allied Powers would fight in World War II and (2) “The Golden Rule,” a 1961 Saturday Evening Post cover, which reflects the artist’s philosophy of universal brotherhood. “As a testament to the power of the image, a mosaic based on the painting was installed at the United Nations Headquarters in 1985” (Saturday Evening Post, February 2, 2015).

Herman Melville’s Arrowhead (Pittsfield, MA)

Melville 1850 purchase of  the farm estate he named Arrowhead because of the Indian artifacts he found in its fields was either “…the consummation of a love affair with the Berkshires that had begun as a boy” (New York Times, June 7, 1998) or a move to be close to his muse, Sarah Morewood, who lived on an adjoining property. A visit here includes a 45 minute tour ending in Melville’s study from which you can, on a clear day, see Mount Greylock which served as inspiration for Moby Dick, perfectly framed by the window above his writing desk.

Where we ate

Nudel (Lenox, MA)

Nudel gets 4.5 stars on both TripAdvisor and Yelp! Its owner and chef, a native of the Berkshires, has been recognized for his creativity and commitment to using local, organic ingredients to create unique and flavorful dishes.

Enso Bistro (Pittsfield, MA)

The menu here is huge – spanning sushi, Asian fusion and hibachi cuisines. Tip: $30 vouchers toward hibachi dinners are often available for $18 (or less if you can apply a sale code) on Groupon.

Eat on North (Pittsfield, MA)

Interestingly, the very center of downtown Pittsfield is the junction of North, South, East and West Streets. Three blocks north (@ 297 North Street) is the aptly-named “Hotel on North” and its restaurant, “Eat on North.” We used the “note to restaurant” feature on OpenTable to score a very nice window table for 2 and enjoyed a delicious dinner; my wife loved their P.E.I. mussels and I thoroughly enjoyed “Mama’s” meat loaf. Tip: While the hotel offers complimentary gated parking behind the hotel for guests, parking on North Street is free after 4:00pm.

About the Author:

I organize things; it’s what I do! I enjoy the natural adrenaline high of travel as much as the next person but I also try to limit the likelihood that the surprises I experience along the way will be unpleasant ones. To this end, I spend more hours than most preparing for each trip. Fortunately for me, I enjoy the anticipation of travel as much as the experience of it. The focus of my trip reports will be to help those who read them to enjoy high value experiences — maximizing enjoyment while minimizing cost. I’ve been a minister, nonprofit agency executive, professor and consultant; my “job” in retirement is planning our next trip. If you would like additional information and/or recommendations, please feel free to contact “The Travel Organizer” via email.

=====

To make sure you receive our latest deals, LIKE our The Flight Deal Facebook Page, follow us on Twitter @TheFlightDeal, Threads @TheFlightDeal or The Flight Deal WhatsApp channel or subscribe to The Flight Deal RSS Feed or Subscribe via Email (Once a Day)

The Flight Deal does not sell travel products or services. We provide you with information about third-party travel suppliers’ offers, and link you to their sites. The information posted by The Flight Deal is valid at the time of publication. However, we have no control over the suppliers, and we therefore do not warrant or guarantee that their offers will not change or become unavailable. Nor are we responsible for their products, services or site content. Please see their sites for their most up-to-date offer information and all applicable terms and conditions.