The Berkshires

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Why The Berkshires:

Berkshire County aka The Berkshires encompasses the extreme western edge of Massachusetts.  It has long been regarded as a popular summer destination for its cultural and natural amenities.

My friend Daniel worked for a hotel chain that was opening a location in the Berkshires. The company was throwing an opening party for friends and family which included a free weekend stay. This was an offer I could not refuse. 

August 12, 2022: The Welcome Party

Due to the spread-out nature of the Berkshires, having a car is necessary to fully experience the region. I rented a car via Kyte, a new rental car company that drops the car off at a location you pick. I arranged to have the car dropped off at the Hoboken PATH station. 

From Hoboken, I was able to avoid much of the traffic leaving NYC, as the path mostly went along backroads. I drove north through New Jersey, crossing the George Washington Bridge and then heading north through Westchester. 

Soon enough, I was heading north along the wooded Taconic State Parkway. Eventually, I turned east into Massachusetts and continued for the final 30 minutes along country roads until I reached the town of Lenox. 

Lenox is a classic New England town with a cute center full of colonial and clapboard splendor. 

The Life House hotel is just to the north of the town. It was described as a writer´s retreat.

The hotel is a cross between a motel and Soho House. The shell of the building is a former Days Inn Motor Lodge. But at the same time, the interiors scream Soho House with the choice of furniture, the scents, the attentive yet cool staff, and the hip crowd. 

The entry lobby, with its high vaulted ceiling and cocktail bar, was the center of all the action for the weekend. It was here I checked in and where meals and drinks were served. I arrived just in time for the first night´s dinner party. Food was served buffet-style outside and included samples from their normal menu. Inside, the cocktail bar was open…and free. While mingling with the crowd, I met most of the leadership team of the hotel chain: the founder/president, marketing, sales, concept design and of course my friend Daniel the head of Food and Beverage. 

As Daniel was still training staff and ensuring that operations worked, he was quite busy running back and forth from the bar to tables to the back of house. Later in the night, he started making cocktails behind the bar. It was obvious from this party that Daniel is not comfortable with even a second downtime. If he was not working on a task, he was chatting with guests and getting drinks. It is this passion and work ethic that has made him a success in this role and will make him an even greater success in the future. 

While we did not have that much time to chat, one of the most interesting conversations we had was on how to design a cocktail menu. Daniel explained that there are only 6 cocktails: Old Fashioned, Martini, Sidecar, Sour, Highball and Flip. Every other cocktail is a deviation of one of these 6. For example, a daiquiri is a whisky sour with whiskey instead of rum and lime juice instead of lemon juice. A margarita is a whiskey sour but made with tequila. A caipirinha is a whiskey sour but made with cachaça. A good cocktail menu (aka one that has a drink that excites a lot of customers), is one that covers all the drink types. Additionally, a good cocktail menu will contain as many of the popular liquors as possible: vodka, tequila, whiskey, gin and maybe now mezcal. Based on the “vibe”, a cocktail menu can tilt in a direction aka have more tequila and sour drinks to represent fun.

The part went until very late, but I decided to go to sleep around 11:30 to rally for two big days of sightseeing. 

August 13, 2022: South of Lenox

I woke up early and started my day with a hike. Daniel recommended the Stevens Glen trail. While just under a mile, the trail wound its way through stunning forests. 

Stevens Glen

I then headed to nearby Tanglewood, an outdoor concert venue that has been the summer home of the Boston Symphony Orchestra for 90 years. Tanglewood also hosts other concerts and has a music conservatory for youths. 

Today, the Boston Symphony Orchestra was rehearsing for a concert with Yo Yo Ma, the famed cellist. By attending the rehearsal instead of the real concert, I got in for about 30% of the price, but the pieces will likely not be played in their entirety. And indeed, that was the case. The conductor made multiple stops during the first piece and chatted privately with the orchestra. 

The final piece of the performance was Enescu´s Romanian Rhapsody No. 1. The conductor was Romanian and felt a great pride to conduct a piece from his country. As the joyous music filled the air, I reveled in the sunny weather on the lawn with the masses. What a perfect atmosphere!

I then drove over to The Mount, the massive home of Edith Wharton. Wharton was one of the most famous American authors of the early 20th centuries and was the first woman to win a Pulitzer Prize. Due to her financial success, she was able to build a massive house. She built the house in 1902 and lived in it until 1911. By this point, her marriage has deteriorated and she decided to move to France, where she lived until her death. 

The house has many impressive rooms, but the highlights were the dining room and library. On the second floor, Wharton´s bedroom and boudoir can also be seen. The house is in a good state of preservation, quite a feat considering its numerous owners over the years including a school. 

The surrounding gardens and forests are stunning and full of sculptures making The Mount a spectacular spot to visit. 

My next stop was lunch at Joe´s Diner in the nearby town of Lee. The diner is nearly 100 years old and was featured in the famous Norman Rockwell painting “Runaway”. The staff might have been there when it opened 100 years ago! They were not so friendly on the surface, but I am sure they have great rapport with longtime customers. I ordered a cheeseburger with blue cheese. 

Next, I drove 5 minutes to High Lawn Farm, the region´s most famous dairy farm. The farm is best known for selling cheeses and ice cream. As entertainment, they let visitors hang out with the baby cows who are so so so so so cute. My favorite cow was named Jojo. 

I then drove south to Stockbridge to visit the Norman Rockwell Museum. The museum contains two rooms of his art and 6 rooms of art inspired by the world-famous pop artist who lived here in the Berkshires. Rockwell´s studio can also be visited as part of a guided tour, but the only openings were too late for me. 

From Stockbridge, I drove 30 minutes south to the border with Connecticut. There, I started the hike to Mt. Frissell. The 5-mile loop started out steep and took me to the summit. However, the main attraction was not the top of the mountain. On the south slope, the trail crossed into Connecticut and a stone cairn marked the highest point in the state of Connecticut. 

Interestingly, this is one of 3 state high points that are part of taller mountains in other states: Black Mesa in Oklahoma and Boundary Peak in Nevada.

Highest point in Connecticut, the south slope of Mount Frissell.

Descending the steep slope of the mountain, I reached a cairn marking the tri-state boundary of Massachusetts, Connecticut, and New York. I then walked back to the parking area completing the 5-mile loop. 

To celebrate, I stopped in for a cocktail in the Red Lion Inn in Stockbridge. The historic inn opened in 1773. While I would have loved to stay for dinner in the beautiful dining room, instead I headed back to Life House for the final dinner/party.  

Dining room of the Red Lion Inn

August 14, 2022: North of Lenox

Today was going to be another busy day of sightseeing. After an early breakfast, I drove 30 minutes north to Mount Greylock, the highest peak in Massachusetts. Mount Greylock is a lone mountain, also known as a monadnock (a geologic term named for a nearby mountain in New Hampshire).

While I would have loved to actually climb the mountain along one of the many trails, in the interest of time I drove to the top. Well…not quite. I had to walk the final 50 meters, which funnily enough were along the Appalachian Trail. 

The summit of Mount Greylock is sprawling. The highest point is topped with a large lighthouse-like monument that itself can be climbed. From here, there are 360-degree views of the terrain. 

The Roof of Massachusetts

The summit also has a historic lodge that functions as a hotel for through-hikers on the Appalachian Trail. 

Coming down the north side of Greylock, I reached the town of North Adams. This industrial town is home to a regionally famous art museum known as MassMOCA. 

The museum is housed in an old print works factory and is one of the largest contemporary art museums in the US.


The collection was VERY impressive. The most famous installations are their collection of 10 James Turrell pieces. But they had a lot more. I spent 2 hours there at my decently fast pace. I´m sure if you are an art person, you could spend an entire day here. 

After a delicious, marinated burger in an old train station, I drove 10 minutes west to Williamstown in the extreme north western corner of Massachusetts. There, I quickly visited Williams College, the top-rated liberal arts college in the entire United States. I cannot imagine going to school there, but I am sure that the campus has a strong culture and lots of traditions to keep things interesting. 

With that, I headed west into New York. 

Final Thoughts:

The Berkshires is an incredible region. With nature, cultural amenities, history, great food, and lots of cute town, it seems to have it all. This is the East Coast´s answer to Aspen, Colorado. There was so much to do and see that I really wish I had a third day. 

I have concluded that the most interesting parts of the United States are the liberal rural areas. I believe that, in general, there is a natural tendency for cities to be liberal and rural areas to be conservative because living in a city requires more cooperation from fellow citizens and more services from the government. Therefore, it takes a special cultural shift to be liberal in a rural area. In the Berkshire´s case, the area is liberal because of the strong influence from Boston and the installation of numerous cultural amenities which draws liberals to stay year-rond. 

Other examples of liberal rural areas are: Mississippi Delta (northwest Mississippi), the Navajo Reservation, Northern New Mexico, the Olympic Peninsula, Vermont, and certain ski towns such as Jackson Hole, and Aspen. 

I don´t know if I would visit the Berkshires outside of the summer since most cultural attractions close, but in season with good weather, it is truly perfect.  

I also need to give a shoutout to the Life House hotel. The room, while cozy, was very comfortable, the food and drinks were delicious and I loved the social atmosphere, which it appears they are trying to preserve even after the welcome party. If you are looking for somewhere central to stay in the Berkshires, look no further than Life House. 


One response to “The Berkshires”

  1. Cathy's Native Ministry Avatar

    We have family in Westport Point area.

    On Mon, Oct 17, 2022, 8:49 PM – Travel Stories around the

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