One of the reason these turn-of-the-century photos of Northeastern towns are so appealing is the presence of elm trees, which make that cathedral arch shape over the street. Even when none of the buildings are removed, the trees are now inevitably gone, as a result of the decimation caused by Dutch elm disease. Here's a picture from the Wikipedia Elm page showing an example from Salem, Mass., in 1910.

From the Wikipedia article on the town: "Arlo Guthrie's court appearance before the blind judge and his seeing-eye dog for dumping garbage as described in the song 'Alice's Restaurant' took place in the courtroom at the Lee Town Hall."

before you intend to comment. [Or, click the links in the caption. - Dave]

Below, a postcard of the Great Barrington Fair racetrack & judges' stand.

Long before Google Earth came around I had a similar photo of downtown Lee, Mass. in my historic trolley photo collection that I thought had been taken about 1902 when the trolley line first opened to Great Barrington.

During a chance visit to Lee in 1982 I snapped the attached photo and was pleasantly surprised when I returned home and found that I had nailed the photo angle pretty accurately.

In retrospect, based on the size of the trees, I'm guessing my photo was taken a few months after the Shorpy image.

.. but the Municipal building remains along with some of the others.

Wish I knew how to embed an interactive image like the smart people do!

Open Google Maps.
Go to the Street View image you'd like to embed.
In the top left, click Menu (the three dots).
Click Share or Embed Map.
Click Embed Map.
To the left of the text box, pick the size you want by clicking the Down arrow.
Copy the text in the box. Paste it into the HTML of your website.

Don't miss it, or else.