A Brief History

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, as the small bridge there was the only crossing of the Mianus River until 1788.

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. Many of these homes still remain both in and around Hillcrest Park, and also south of the town of Old Greenwich.

Eight of Sawyer’s original named houses are located within present Hillcrest 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, and The Ledges  at #107 Hillcrest Park Road, as well as Breezemont at #9 Hillcrest Lane.

Sawyer’s Buena Vista, a large Mediterranean-style villa often referred to as “The Castle,” was at the base of Hillcrest Lane until early 2015, when it was demolished and developed into the new development on Hillcrest Lane in 2018-2020. In addition, Sawyer’s Stony Crest is nearby, with a Palmer Hill Road address. Hillcrest Hall, Storm King, Brier Cliff and The Gables, along with other original houses 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 #41, #60, and #105.  On Ricki Beth 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

For a more detailed history of Hillcrest Park:

We are indebted for this 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.” Additions added by Dr. Zachary Linhart. For questions or additions to our wonderful history, please email us at hillcrestparkct@gmail.com.