What’s in a Name – The Serpentine Tale of Inningwood Road

Inningwood Road at its terminus in Ossining, looking east from Pinesbridge Road. Photo by Robert Brum

Bicycling the quiet back roads is an ideal way to catch glimpses of what Westchester was like before the county became part of The Suburbs. The old farmsteads, ponds, and woodlands that one might miss from behind the wheel come into focus while on a bike ride. 

One of my favorite bike rides includes parts of Inningwood Road, a roughly one-mile-long, well-paved and lightly trafficked street stretching between Route 100 in Millwood and Pinesbridge Road in Ossining. 

One of Inningwood’s highlights is Maplehurst Farm, originally known as the Conklin-Chadeayne Farmhouse. Now a private residence, Maplehurst was built around 1760 and saw previous duty as a dairy farm and school, according to the New Castle Historical Society. 

Not far from Maplehurst is Snake Hill Farm, once home to mules that pulled stones during the building of the New Croton Aqueduct, according to the historical society. Snake Hill Farm had long-horned Scottish Highland cattle grazing on the property as recently as 1995. 

Inningwood was originally named Snake Hill Road, which seems appropriate given its serpentine layout and the steep hill at its Millwood terminus. But apparently real estate agents found that name too off-putting to prospective buyers. So they came up with Inningwood — a comingling of Millwood and Ossining. 

Do you have a local place name you’d like to see in this feature? Email me at editorial@rivertownsmedia.com with “What’s in a name” in the subject line.


  1. Not sure if this would make for a good article – but the topic of what authority or approval is needed for naming streets, towns (like how did N. Tarrytown get changed to Sleepy Hollow), etc. It’s just coming up a lot of course about who authorizes name changes of bridges — Tappan Zee / Cuomo is what sparked it. So even if it’s just about how North Tarrytown got changed to Sleepy Hollow would be a cool piece without getting political. I love the name change – makes the area seem magical, and I bet it’s good for tourism. I like being able to say I was born in Sleepy Hollow, lol (as were many in the area – that’s where Phelps is! 😉

    Just an idea – or, I could probably google it, but Robert’s writing is so great it tells a story.

  2. Hi, Cheri –

    In the case of the replacement bridge’s name, the governor appointed a committee to come up with a recommendation. The committee recommended naming it after the governor’s father. I’ll leave it at that.

    In the case of North Tarrytown’s renaming, this is from the village’s website:

    In the 1980s it was proposed that the village rename itself Sleepy Hollow in an effort to reconnect with its famous past. In 1996 the village voted for the renaming, the same year that the GM plant closed its doors.

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About the Author: Robert Brum