The Berkshires Blog

2 New York City Teachers Find Home in the Berkshires

By Wendy Benjamin

It seems like only yesterday that we were neophytes to the Berkshires. It began 20 years ago with a few weekend visits from New York City to a friend’s home in the quintessential New England town called Monterey.

A typical weekend was spent cross country skiing, visiting the Clark Institute, enjoying a few delicious meals in town, and ending the days in front of the fireplace planning our next visit.

My budding love with the Berkshires began with the obvious; the extraordinary beauty of the surrounding mountains and all the cultural offerings was just the tip of the iceberg.

Spending time in a liberal minded and inclusive community was of utmost importance to me since my life’s journey is shared with another women. Being a New Yorker, I needed a place that had panache but yet maintained a small town feel. I found all these prerequisites right here in the Berkshires.

A life changer happened on one of those weekend visits. My partner and I were looking at houses for sale in The Shopper’s Guide. On a whim, we made a phone call and set up an appointment to look at a house that was for sale in Monterey. The house was a neglected one-bedroom cottage on two and a half acres of lovely but terribly unloved property.

My partner and I looked at each other and we both asked, “Can we buy this place, will we be ale to make it livable without breaking our necks on the ripped linoleum floors, do we really need a country home?” I saw the twinkle in my partner’s eyes and I knew the answer was yes! We took the plunge and made a plan to renovate in stages. Here we were, two New York City teachers with a country home. WOW!

Stage one of renovations was completed two years later. We found ourselves driving up most weekends throughout the year and we soon discovered that every season in the Berkshires is unique and beautiful.

Fall is filled with colors, apple picking, hiking, and that little chill in the air gives you an excuse to put on a sweater and start the fireplace in early October.

Spring is filled with getting the garden ready, dusting off the patio furniture and listening to the loud chorus of birds outside our window.

Summer means two months off from school, swimming in Lake Garfield, picnics on the lawn at Tanglewood, dance at Jacob’s Pillow, hiking on the never ending trails throughout the area and just having a terrific time!

Winter perhaps, is the season that most surprised me. Never a lover of cold weather, I must say, it is different in the Berkshires. Yes, it is cold, but so incredibly beautiful. The light in the sky is magnificent this time of year and if you wear your winter gear and get outside to enjoy, it is life affirming.

Now, to bring you up to speed, 20 years have gone by, we are now planning stage four of our renovations, my partner and I have a nine-year-old son and we will become full time residents of the Berkshires in a year and we can’t wait!

PS: If you are ever up one weekend and are looking in the paper for something to do, beware, you may find a neglected cottage and your life may change forever!

For more information about Berkshire Real Estate click here.