I assume in your profile that you're on the Cape?

Not that I'm from MA or anything but check out

www.bikemaps.com

They are Rubel and publish very nice bike suitability maps of the entire state, depending on how long you have, you could ride out to the Berkshires, or ride north into the White Mountains or Ride to Maine... Sheesh, lots of options! How long do you want to go? You could ride and take the ferry to Martha's Vineyard or so and explore the islands for a short tour.

You're post is very wide ranging What timeframe are you looking at, it's getting dark early and if you go north, it's getting quite cold at night, if you're a camper.

Jay