Starting from an intersection with Sprout Brook Road at Continental Village just north of the Putnam-Westchester county line, it ends at an oblique junction with US 9 east of Garrison.

As the least improved section of the original Albany Post Road,[1] it was added to the National Register of Historic Places (NRHP) in 1982.

Some of the milestones placed during the early years of American independence to more accurately calculate postal rates are still present and have been preserved and restored.

Old Albany Post Road passes through heavily wooded and lightly populated country along the southeastern edge of the Hudson Highlands.

From there it takes a west-northwestward, meandering course at first, narrowing almost to one lane at some points and climbing steadily to where the Catskill Aqueduct crosses, but soon bends to the north-northeast and widens.

Beyond, the road remains mostly straight and northwestward, eventually returning to more wooded country along a ridgetop where the southwestern corner of Clarence Fahnestock State Park is nearby.

The colony eventually became the English Province of New York, and in 1703 its legislative body provided for the postal road to be a "public and common general highway" along the same route, starting in Kingsbridge and ending at a ferry landing in present-day Rensselaer.

[3] The best-known, John Warren's Tavern, was built in 1756 and remains in use today as the Bird and Bottle Inn restaurant at the junction with Indian Brook Road.

He retreated to what was named Continental Village after the Battle of White Plains and the road remained fortified and defended throughout the war, used as a supply route,[1] and often traveled by Washington and his officers.

[1] The completion of the Hudson River Railroad to Albany in 1850 made the road obsolete as a commercial and postal artery, and stage service ended.

The road provided access to a section of the Catskill Aqueduct, and shops, housing and bars were built along it to shelter and serve the construction workers.

Homes and farms along the road were electrified in 1935 due to the efforts of the newly created Rural Electrification Administration, adding utility poles to the landscape.

[1] Following its NRHP listing, a group called the Old Road Society of Philipstown (ORSP) was formed to help preserve and promote it.

Proponents, many near the road's southern end, cite public safety concerns such as inaccessibility for police and fire vehicles during washouts in heavy storms like the April 2007 Nor'easter, which left craters four feet (1.3 m) deep in front of some driveways.

The Philipstown Board cited three reasons for paving; the cost of maintaining dirt roads are too expensive, degradation of water quality in nearby streams, and safety.

Sections that the town wants to pave include two important historic areas; Saunders Farm and the hill that runs north to the famous revolutionary era Bird and Bottle Inn.

[8] It was also pointed out that the Town of Philipstown could be in violation of state bonding laws if they were to pave as proposed with merely a thin coat of asphalt and no substructure preparation.