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Section l

The first section shows the western portions of the Croton Turnpike (now Croton Avenue and Somerstown Road) and Old Sing Sing Road (now Ryder and Pinesbridge roads) in the town of Ossining. At the point marked B, the turnpike branches eastward from the Highland Turnpike (now Highland Avenue) in the village of Sing Sing (now the village of Ossining). At point C, Old Sing Sing Road in turn branches off to the northeast, passing through the extensive farms of the Ryder (here spelled Rider) family.

Section 2

The central section of the map focuses on the west end of New Castle, from the border with Ossining to the center of present-day Millwood. Old Sing Sing Road (now Pinesbridge Road) runs roughly parallel to the Croton Turnpike (now Somerstown and Saw Mill River roads). Near the center of the section, Inningwood Road extends southeast, connecting the two main thoroughfares.

Some of the homes shown here still exist. They include the Arthur Williams and Winthrop Hoag houses on Pinesbridge Road and the Nathaniel Conklin house on Inningwood. The Tompkins family farms on Pinesbridge now form the core of the Hudson Hills Golf Course, and the Tompkins family graveyard is preserved between two of the fairways.

No longer in existence is the Granite House, which was constructed a few years later on the site labeled Simeon Partelow Tavern in the lower right corner of this section, at the intersection of the present-day Saw Mill River and Shinglehouse roads and Route 120. The Granite House would become a major stagecoach stop and community center for many decades, and remained a historical landmark of Millwood until its demolition in 1993.

Section 3

The third section of the map shows the eastern portion of Old Sing Sing Road (Pinesbridge Road) as it passes from New Castle into the town of Yorktown and doubles back on itself to intersect at point A with the Croton Turnpike (Saw Mill River Road) on the way to Pines Bridge and Somers.

Proceeding from the lower left to its end at Old Sing Sing Road is Shinglehouse Road. At the intersection is shown the home of James Cornell, the shingle house that gave the road its name.

Farther east on Old Sing Sing Road is shown the “land of David and Samuel Chadeyne.” The name later came to be spelled Chadeayne, and the house still exists, at the corner of Chadeayne and Pinesbridge roads.