The pictures above are from glass negatives in the Bancroft Library Hopedale history collection. They were evidently taken by Edwin Darling who lived at 54 Freedom Street.
The picture at the top of the page is a bit of a mystery to me. It looks toward the Northrop Street side of the park, and also shows part of Park Street. The two Northrop Street houses in the picture are still there, but the Park Street houses are gone. The Park Department history says “Park St. entrance cut through Park Wall” in 1916. However, the picture shows the entrance there in 1901. I’m sure it’s not a mistake on the date. None of the Darling pictures are dated after 1910. Also, if the picture was from 1916 or later, the Park Street School would be seen in it.
After giving the matter some thought, it occurred to me that there are two park entrances on the Northrop Street side, and they probably weren’t both created in the same year.
The photo below is from an album at the library. The pictures in it were probably also taken by Darling. I’ve included it so you can see where the other pictures were taken from. The house at the left was the Roper house at 50 Freedom Street. The one next to it was the Darling house. The white house in the middle was a duplex built by Henry Patrick for his employees. Mrs. Darlilng’s parents lived in the one to the right of that. This is obviously a very early view of the park. I don’t think it could have been taken any later than 1900.