If you are looking for rail trails, I like the Nashua River Rail Trail that starts in Ayer which is just up 495. The Blackstone River Rail trail is also pretty nice but shorter and just over the line in RI. Go to massbike.org and you can look up the various trails and places to ride. It gives a description and usually a map. The sevenhillswheelmen.org also has group rides you can join, starting at level D (easy) and ****'s easy rider group C rides easycrider.com