This appears to be a customer that has won some windshield washer fluid at the gas station operated by the United Cooperative Society. The station was located at 5 Waltham Street.
Walter Boeske and an unknown customer. Boeske Brothers Rambler auto dealership was located on Brown Street (Rout 27). Rambler stopped producing automobiles in 1969, so we assume this photo is prior to 1970.
This is the original location of Tutto's Bowling Lanes at 24 Main Street before it relocated to a larger facility in the rear of this building in 1964.
A group of students attend a ceremony to plant a tree in front of Emerson Junior High School (Fowler School, Summer Street). Possibly Arbor Day? Holding tree: Tommy Sheridan?