(Courtesy of their website):

Established in 1932, Bousquet Mountain is the oldest existing ski area in The Berkshires. Before it was a ski area, the property was a mink farm belonging to Clarence J. “Clare” Bousquet.

After his mink farming operation failed during the Great Depression, Bousquet allowed the Mount Greylock Ski Club to cut a 750 foot ski slope up to the northern summit, and Bousquet’s Ski Grounds was off and running.

The installation of Bousquet’s first rope tow in1935 brought more visitors, and prompted Clarence to increase the ticket price from 25 cents to one dollar.

History and more information can be found on their website.

Pittsfield Tire was a renowned tire dealership in Pittsfield. Pittsfield Tire and Battery was located in West Street, at the SE corner with center. I couldn’t find much out about the business, but a Facebook group that I belong to, blew up about which building it might have been.

One helpful comment:

Pittsfield Tire and Battery was originally founded by Howard Spaulding Babbitt, who was also a longtime member of Mystic Lodge of Freemasons.

If you know more, I’d love to hear it.

So much history of this amazing inn can also be found on their website. The Red Lion Inn, located in Stockbridge, Massachusetts, has a rich history dating back to the late 18th century. Originally established as a small tavern in 1773, it grew in popularity and expanded over time. It has hosted notable figures such as Nathaniel Hawthorne and President William McKinley. Treadwell, the inn's adjacent restaurant, was named after a prominent family that owned and operated it for several generations. Today, the Red Lion Inn continues to thrive, offering charming accommodations and delicious dining experiences, while preserving their historic charm for guests to enjoy.

The Jug End, located in Egremont, Massachusetts, has a historical significance as a former farming community. In the early 19th century, it became known for its production of stoneware jugs, hence the name "Jug End." Over time, the area transitioned from farming to recreation and conservation. Today, Jug End State Reservation offers hiking trails, scenic views, and outdoor activities, preserving the natural beauty of the area. The Jug End Barn, a historic building in the reservation, serves as a cultural center, hosting events and exhibitions to showcase the region's heritage.

On August 13, 1936, the BSO gave its first concert in the Berkshires, at Holmwood.

Tanglewood, nestled in the town of Lenox, Massachusetts, holds a significant place in the world of classical music. Established in 1937, it is the summer home of the Boston Symphony Orchestra. The magnificent outdoor venue attracts renowned musicians and hosts an annual music festival, featuring performances of symphonies, operas, and chamber music. The picturesque grounds of this renowned venue has welcomed virtuosos such as Yo-Yo Ma, Itzhak Perlman, and James Taylor. Read more on their site.

The Greylock Bank in Adams, Massachusetts has a storied history dating back to 1869. Founded as Adams Cooperative Bank, it aimed to provide financial services to the local community. Over the years, the bank expanded its operations and established a strong presence in the region. In 1991, it merged with Greylock Federal Credit Union, adopting the name Greylock Bank. Today, Greylock Bank continues to serve Adams and the surrounding areas, offering a range of banking services while maintaining its commitment to community support and customer satisfaction.

England Brothers was founded on North Street in 1857 as England and Brother by brothers Moses and Louis England. By 1875, Louis had left the partnership and the dry goods business was known as M. England. Moses England's two eldest sons, Benjamin and Simon, were employed by the business in 1882. During its 131 years on North Street, the department store would celebrate many firsts — the first delivery truck, the first store with an elevator and the first escalator in the county. (courtesy of The Berkshire Eagle). Article on England Brothers

I currently cannot find any information about this little amazing stop along Jacob’s Ladder in Becket, Ma. If you have any knowledge, hit me up as I’d love to supply the history to readers. Thank you!

The Cove Bowling in Great Barrington, Massachusetts, has a rich history as a beloved community gathering place. Film makers, the Coen brothers, attended Bard College at Simon’s Rock in Great Barrington and hung out at the Cove. It is thought to have influenced their cult creation, “The Big Lebowski” in 1998. You can read more here but it looks like it’s up for sale and the town of Great Barrington is getting a say. Article

In 1910, Harris Fahnestock Jr., a stockbroker from New York City, began to build a summer home named “Eastover” for his family on 1,500 acres of land in Lenox, MA.

For the next 62 years, Eastover served as a year-round recreational family resort, and also housed one of the largest Civil War collections in the country. This resort became an icon in Western Massachusetts and hosted generations of graduation parties, corporate picnics, reunions, and also served as a popular BYOB dance and music venue.

Courtesy of their website. History

While skiing at Oak 'n Spruce in Lee is perhaps best known for a rope tow slope that operated onsite for about four decades (starting in 1947-48), a much larger ski area was once planned by owner Frank Prinz down the street.

I purchased this run down property in the winter of 1946-47 and started major renovations and opened up as a resort "Oak n' Spruce" the weekend of May 17,1947 . to a full house. For accommodations there were two dorms with double deck bunks...The "Queen's" room that held 32 women and the "King's room" that held 28 men, plus 4 rooms with private bath, renovated kitchen, dining room with rustic tables and benches to hold 80 persons,, lounge,, registration desk and office and sleeping room for myself. The basement was renovated to a recreation hall. - Frank Prinz

More history here

I can’t find too much information about the hotel as it was, but there’s this amazing postcard from the time here and here. It’s currently Allegrone Berkshire Design Center and you can still see a bit of the historic roof in the new building.