White's Corner, where the Starbucks now stands, was an important stop on the Boston and Worcester trolley line. From here you could take the line over the causeway to Marlborough and Hudson. The tracks were ripped out and sold for scrap during WWII.
These mill buildings, built 1860-1900, stood where the MBTA parking lot is now located. They were intact until the 1970s until the Town authorities condemned them and sold off the bricks. One can only imagine how wonderful it would be to have these buildings today as mixed residential/commercial units.
You don't usually associate a "square" with Southborough, but obviously residents in the 1880's and 90s did. This was the view from the Centre Store with the porch of the Winchester Tavern just visible at the right and St Marks church just visible at the left. The Fay school demolished both the Tavern and the store in the 70s to build their dining hall. The Library now sits on part of the Square land.