NYCDEP has a very fine-scale impervious surface layer for their watersheds. It’s not publicly available, but I think they’re open to data requests.
Brendan Murphy
Dir. of Stewardship
Westchester Land Trust
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NYS Clearinghouse has a 1 ft DEM for Columbia and Rensselaer Counties. I use it for verifying georeferenced surveys. I can pick out stone walls with it. It might be adapted for your purpose.
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Ulster County has 1m resolution landcover that was created by UVM in 2013 for mapping the Delaware River watershed, but they extended it to cover all of Ulster, which is nice. https://www.pasda.psu.edu/uci/DataSummary.aspx?dataset=3167
The Chesapeake Bay Conservancy mapped all of that watershed similarly at 2m resolution a while back (also 2013/2014), which covers the Susquehanna portion of NY, but won’t help in the Hudson Valley.
-Dave
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Conservation and Land Use Specialist, Hudson River Estuary Program/Cornell University
New York State Department of Environmental Conservation
21 South Putt Corners Road, New Paltz, NY 12561

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Westchester County’s GeoHub portal (https://gis.westchestergov.com/) also has all the parking lots as a layer in their planimetric data that you can download.
You might try asking for planimetric data from the other NY cities/towns/counties you are looking at (I don’t know if any of the others have their planimetrics online or not).
-Dave
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