APRS tracks for my rides around Poughkeepsie in early November 2015:

Turning on the topo data and squinting at the Red Oaks Mill area:

The topography isn’t in my favor, with two ridgelines between Red Oaks Mill and the two APRS nodes near Poughkeepsie. APRS coverage southwest of Red Oaks Mill along the Mighty Wappingers Creek (basically, Vassar Road) ranges from spotty to nonexistent, because that route has even worse topography.
Seems to me an APRS iGate in Red Oaks Mill, running Xastir (perhaps headless) on an RPi, conjured from my heap (perhaps with a shiny new TNC-Pi atop the RPi, rather than an ancient Kantronics KPC-9612), and using a vertical VHF antenna in the attic (because lightning), might improve the situation.
That whole project continues to slip into the future, but at least I have more motivation and linkies…