Welcome to the bucolic Mid-Hudson Valley!
The Quick Reference links page at the top of this forum's main page has a bunch of Metro-area links. The one that has the most information about the Dutchess county area is:
- Bike Hudson Valley with rides, resources, and links
You might want to head over to Beacon Cycles on Main and ask where they ride. The two bike shops in Wappingers also do weekly rides (http://bikeway.com/
). Bikeway has a Saturday morning ride that should be heading outside pretty soon (hopefully). The first Saturday of every month is newbie friendly.
The direct route to Pok is up 9D which, as of this morning, looks like a war zone :-) It's the only North-South route that close to the Hudson so traffic can be heavy (and fast) at times and the shoulder is crumbly.
The local bicycle club is the Mid-Hudson Bicycle Club (http://midhudsonbicycle.org/
). I'm not a member so, I can't tell you how active they are. I've only been cycling regularly since last Spring.
Over the last few years the number of cyclists on Dutchess-area roads has been increasing - if ever so slightly. Drivers are on the polite side if it's not rush hour. Most roads feature the occasional garbage truck and 18 wheeler.
You can sometimes cut through neighborhoods to avoid traffic but, most developments are designed as islands and you often exit near where you entered. And maybe this is just me but, they also seem to be built on top of hills :-) We have a preponderance of roads that feature words like ridge, hill, top, view, and mountain.
If you head east, northeast, and north of Poughkeepsie things start looking downright rural again and there's less traffic.
Avoid or limit your time on routes 52, 82, 9, 376, 28, 44, 55, 94. They are all main connector roads and are heavily used. They look really tempting on Google maps and you can't always avoid them -- 52 and 82 especially since they take you way east or way northeast. Just limit your time on them if you're by yourself.
Looks like there's a nice 10 mile loop from the train station out to Glenham and back. If you add a leg down 9D to Cold Spring that'll be 20 miles.
Good luck and post any good routes you find.