Enveloped today by the Hallowell subdivision, Rockland grew from a log core built in the early 1800s. Around it Benjamin Hallowell built a double house that son Henry Clay Hallowell adapted as a Quaker school. Here Benjamin conducted numerous experiments in progressive agriculture and had his observatory, library, and carpentry and smith shops. Rockland's name derived from the claim that one could walk from the front door to the farm boundary without ever stepping off the many fieldstones. St. Peter's Catholic Church occupies land that once was part of Rockland.

Rockland's lawn provides a setting for the Hallowells c.1905. From left, front: Eliza (Chichester), Cornelia (Bentley), and Edith; behind, Elgar, Frank, Mary (Stabler), and Robert. According to historian Farquhar, Rockland's Hallowells continued the legacy of Benjamin, making the home "truly the fountainhead of neighborhood culture at that time."