Brief History of Hillcrest Park

We are indebted for the following information to Geoffrey Lynfield, a former Park resident, and his extensive research on Joseph D. Sawyer, the author of “How to Make a Country Place (1914), and on subsequent Park landowners in connection with his “Hillcrest Park, History of an Old Greenwich Neighborhood.”
During the American Revolution, American soldiers made camp on Palmer’s Hill, a strategic high point which then afforded clear views down to the Sound. Palmer’s Hill Road was then part of the King’s Highway, the post road linking New York and Boston. It is likely that George Washington crossed the Mianus River at what became known as Dumpling Pond Bridge for a mill owner’s patriot wife who reportedly threw her dumplings into the pond rather than serve them to British soldiers. The small stone bridge, whose foundations date back to 1688, carried all Boston Post Road traffic until 1788. The Post Road (Route One) was then relocated to less hilly terrain following construction of a larger bridge over the Mianus.

In 1886, Joseph Dillaway Sawyer (1849-1933), a textile executive who commuted between New York and Boston, came in search of a convenient country place. He paid $8,500 for the widow Sabina Bowen’s 78-acre farm atop Palmer’s Hill, most of it located in the Town of Greenwich, moved her century-old house by ox cart to what is now #53 Hillcrest Park Road, remodeled it, and called his new property Hillcrest Farm. After a fling at dairy farming, Sawyer turned to real estate development, seeing a potential in building large summer homes for New Yorkers.

At one time Sawyer owned 250 acres of land in Greenwich and by 1911 had built some 30 substantial residences, most of them to his own designs, in this area and along  the shoreline of Long Island Sound.

Eight of Sawyer’s named houses are located within present Park boundaries. They are Hill Top  at #1 Hillcrest Park Road, Brillewood at #39, Stonehenge* at #64  once owned by bandleader Guy Lombardo, Sky Rock  at #72, Cliffmont at #97, Croftleigh at #80, The Ledges  at #107 & Breezemont  at #9 Hillcrest Lane.

Sawyer’s Buena Vista, a large Mediterranean-style villa often referred to as “The Castle,” and his Stony Crest are nearby with Palmer Hill Road addresses. Hillcrest Hall, Storm King, Brier Cliff and The Gables, once located in the Park, no longer exist.

Over the years Sawyer-built estate outbuildings have been transformed into private residences, many retaining picturesque features. On Hillcrest Park Road they include #60 and #105.  On Rickibeth Lane, named many years ago for a granddaughter of a Croftleigh owner, there are #11 and #7 . The latter, once a stables-carriage house with ballroom, was said to be a casino in the “Roaring Twenties” frequented by New York’s colorful Mayor Jimmy Walker.

In the 1930’s, architect W. Stuart Thompson designed several attractive colonial-style brick residences on Hillcrest Park Road. They include #65, #69 , #73 , #87  and #93. As prized one-acre lots became available in our private association, other property owners built comfortable homes in various styles.


* plaqued by The Historical Society, Town of Greenwich

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