Gregory's Orchard

Red area here known as Gregory's Orchard

The traditional and original name of The Hattertown District was Gregory's Orchard. The Gregory's Orchard school district created in 1788 included this corner of town with its boundaries against modern-day Easton, Redding and Monroe. From there, the district ran roughly to the bottom of Castle Meadow Road and over to the intersection of Mt. Nebo and Purdy Station Road. The short stretch of road with three homes on the western side of the Hattertown Green was once called Gregory's Lane.
I always wondered who “Gregory” was and where the orchard was located. There is no written history on the origin of the name or the orchard that I know of. As a surname, the name "Gregory" does not appear in town records until the 1720s, but in the earliest land records of 1712-1713, the area is still referred to as Gregory's Orchard.
This ownership of land predated the purchase and settling of Newtown (1705-1711) by a number of years to be cleared land with a mature enough orchard to become a landmark location. The earliest history of Newtown began in Stratford, when it was a large plantation that reached this far north. Stratford was first settled in 1640, with the northern boundary being set at "12 miles from ye sea." This boundary remains unchanged to this day and is the current town line between Newtown and Monroe.
I have identified Samuel Gregory (1646-1702) of Stratford as the most likely person to have been the Gregory that the orchard was named after. The facts I discovered seem to make it a strong possibility. In 1646 Samuel Gregory was born in Stratford. His father, Judah Gregory, died five years later. About the year 1665, Samuel Gregory and his stepfather, Henry Summers, bought land directly from the Indians in what was then Stratford, built log homes and became the first settlers of what would later become Bridgeport.
When land of Stratford Plantation was purchased from the Indians, there was a mutual agreement that the Indians would retain the right to hunt and fish and use the land in the northern parts. Eventually, conflicts arose as the settlers also went further into the land to hunt, and in May of 1671, the Indians quitclaimed their right to the lands in Stratford in a final purchase.
Signing the document that opened the northernmost point of Stratford to settlement were the Pequannock Indians Mascot, Nesumpaw, Sasapin, Shoron and Takijma. The payment was made by "20 pounds of lead, 5 pounds of powder and 10 cloath coates." Shortly after this agreement was a time period of increasing conflicts between the Colonists and Indians that led to King Philip's War.
There was great fear and caution during that time to not create greater difficulties with the Indians and to assemble the settlements closer together in a manner of protecting against attacks. The men of Stratford opened these northern parts of their boundaries, dictating that the right of possession of the lands belonged to the earliest settlers of the plantation first. They were free to choose and claim land in the northernmost parts of Stratford, but they could not build structures or fences and could not settle upon them.
Sometime after 1671, Samuel Gregory would have ventured into the countryside and claimed his land parcel that straddled the border of modern-day Monroe and Newtown. Intentionally or not, the land he claimed extended beyond the boundary and into land that would become Newtown. To mark his land, he planted an orchard, and it became a landmark location on the corner of Jet Brook Road and Castle Meadow.
The location of the orchard is provided in a land deed of the early 1800s that identifies the orchard as once being located on the eastern side of Jet Brook and along Castle Meadow. Aerial photos of 1951 show an orchard on the corner of this land near its intersection with Jet Brook Road. Presumably, this was a tradition and nod to the location of Gregory's Orchard.
The English settlers naturally followed existing Indian trails that led further into the interior. The pattern of early land transactions, language used and other clues strongly indicate that Hattertown Road was an existing path when they first arrived. This path would have connected Hattertown Road as we know it by way of Jet Brook Road.
It is not possible to prove Samuel Gregory's ownership of land in this area with written record, as records did not exist for this informal land claim. However, his will, dated 1702, states that his children may retain his petitioners’ rights (land claims of first settlers) in both Stratford and Fairfield. Records show that Samuel Gregory had moved his home lot as far north as Tashua in Trumbull, and also owned land in "Bare Hills" (Bear Hill Road, Newtown ) before 1700.
Also mentioned is a land parcel that was his "riding ground" for riding horses. Where Hattertown Road meets Judd Road, there were once large sand banks left by glacial activity. This area is just below Jet Brook Road, and its sand deposits would have possibly provided a good riding ground for horses.
Both uses of orchard and riding ground would not require fencing or structures but would also mark ownership by its landscape and purpose. The land eventually went unclaimed or abandoned after Samuel Gregory's death in 1702. There are no records of its sale by the family in Stratford or Newtown. The orchard was known as a landmark location for well over 200 years.
The 1931 map here shows that Jet Brook Road was the original primary path of Hattertown Road and was once State Highway 161. The black and white photo is a postcard from c.1915, showing the intersection of Judd Road looking west to Eden Hill while traveling towards Newtown on Hattertown.