Stockbridge, MA: Wintertime in the Berkshires, Pittsfield, Massachusetts

If the winter of 2015-2016 has been any indication so far, you can’t necessarily plan on an east coast ski weekend away going as, well, planned. With record high temps making it impossible for mountains to make snow, many people lost out on pre-planned ski weekends to warmer, balmier climates. Or, as just with this past weekend, quite the opposite! With record low temps – think negative 20 degrees – coming just in time for Presidents weekend in the New York area and beyond, many people were at a loss as to how to approach their long-awaited holiday ski plans, including us. But with a little research, we came up with alternative plans that proved to be just as fun. We were headed to the Berkshires to Jiminy Peak in Hancock, MA, but we opted to spend most of the weekend in Stockbridge, MA. And what a gem this little New England town is. In some ways I’m sort of glad it was too cold to ski!

To give some background, we had rented a house through Airbnb in Canaan, NY with two other families. We couldn’t stay at Jiminy Peak because we were arriving on a Saturday, and like most mountains, they required a Friday – Monday stay for the holiday weekend. So we found a spacious house in Canaan, close to the border of MA and about 20 minutes from Jiminy. We have been having luck with Airbnb ski rentals recently, as seen in another post on the Berkshires here. Perched up on a hill overlooking the countryside and lake below, we had incredible views, especially at dawn and dusk. The house was equipped with a big wrap around bar and stools, kitchen with wood-burning stove, a “great” room with lodge-type feel, as well as a basement with large screen tv for the kids. It was perfect for our group. But with the biting cold and excruciating windshield, it took a long time for the house to fully warm up. It’s the type of house we could have lounged around in all day if it was just quite warm enough, but since it wasn’t, we decided to make Stockbridge, MA our destination for most of the weekend. And who are we kidding – with this crew, meaning my family, we weren’t going to hang out all day at the house anyways. If it wasn’t going to be skiing, it was time to go exploring! ...... (follow the instructions below for accessing the rest of this article).