WHAT WE DID
We rejoined Route 100 and kept heading south, then followed 8 down through North Adams, Pittsfield and Stockbridge to Great Barrington. Again it was an easy, scenic, interesting drive, though Pittsfield came a bit of a sensory shock after the bucolic countryside we had become used to.
We stayed at The Briarcliff Motel. This was outstanding! Richard and Clare are such amazing attentive hosts!!! The accommodation is simple, stylish, comfortable. The complimentary continental breakfast is excellent with lots of homemade and local selections. Highly recommended!!!!!
We had a built in sightseeing day in the Berkshires and Richard and Clare were very helpful with multiple suggestions. We are both avid readers so our sightseeing took us back into Vermont to Bennington for Robert Frost’s grave (and Stone House Museum which was closed for the season). At the Bennington Museum there was a wonderful Grandma Moses exhibition as well as other interesting historical sections. On our return trip we stopped at Arrowhead, Herman Melville’s home (also closed for the season). Our sightseeing drive wound its way through many back roads so that we visited Stockbridge, Lenox, Lee and Williamstown.
The first night we were here we ate at the Barrington Brewery. And the only drawback was that it was so enjoyable that we ate here again the second night (yes, we should have been more adventurous! Especially as it was not quite as good the second time.)
WHAT WE WOULD CHANGE
We weren’t enticed by anywhere in Woodstock to have breakfast before we left. Big mistake. Ohhhhh I need a strong coffee to start the day and there was a scarcity of places to stop.
Our second visit to the Barrington Brewery was not quite as good (very busy so maybe that had an impact on the quality) Yes, we should have been more adventurous!
It might have made sense to have changed our route south : from Wilmington head west on 9 to Bennington and then south on 7 (as you can see in the “what we did” in a way we doubled back on our tracks on our sightseeing day … but then again, we did it at a slow no-rush pace). This would have meant that our sightseeing day could have headed off in a different direction (more of the Berkshires? The Litchfield Hills? Across to the Catskills?).
Loved our stop here … and we never got to check out all those covered bridges, Clare!! So I wouldn’t hesitate to add an extra night here … there was a lot of exploration to be done and the Briarcliff is an excellent base!