You may want to consider the NY Parkways Erie Canal ride. It is 400 miles, but you never do more than 63 miles in one day and it is quite flat. It has a SAG wagon to carry your stuff and food (plus 2 snacks a day!). It is a camping tour so you will need a tent. Best of all there are over 500 people doing this so you are sure to find a group of like-minded friends. Best of all is was quite cheap about $ 700 bucks for the whole week. I took this as my first fully supported tour and have not gone on another tour since this one was run so well. I expect to be dissapointed by another tour group.