Being an avid windsurfer for over 30years now on the Chessy, I'm always looking for an opportunity to sail, even in colder weather. That being said, CBOFS
http://tidesandcurrents.noaa.gov/ofs/cbofs/wind_forecast.shtml
has been very accurate in their forecast in the past. However just receintly the forecast display has changed (they're not showing the wind arrows over land anymore, not sure why?), and I'm wondering if their model has as well, because the past (4) times I have sailed their forecast was low for wind speeds. Before they were almost spot on every time.
Sailing in the late fall with colder water, southerly's generally don't reach the water because of decoupling due to a cold marine layer sitting and not mixing with the warmer air.
W/NW with colder air will jump right down on ya and be quite gusty especially when clouds are in the mix as they usually are. Last week on the Back River it would gust to 35 and then the lulls would be 0, difficult to sail in.
The Northerly's can be good cold dense consistent air to sail in this time of year when full sunshine is present.
Easterly's generally mean rain which will vary the wind, unless it is a fetch (strong high in New England) than out on the coast you will get a very consistent flow.
With any forecast timing is everything.