Rides for overweight unfit people?

Slow progressions are best for anyone who is unfit, whatever the exercise or activity. Your body and mind needs to acclimatise to the work you are asking it to do over a number of weeks. You need to feel success by setting small goals and working forward. Setting unmanageable goals and failing is no encouragement.

I'm sure that this applies to many people, Shoosh, but I doubt very much that it applies to 'anyone who is unfit'. To me, the Dunwich Dynamo has always been instructive. Year after year, I've seen extremely unfit people start it on unsuitable bikes and somehow get to Dunwich, all of 116 miles, plus extra miles incurred through getting lost, carried along by the friendly atmosphere and because they are pretty much guaranteed to find nice people to ride with. Yes, it's probably going to be a shock to the system, and they might take a while to recover, but the sense of elation felt at the finish is enormous. I know of one case in which you could say that it had been life-changing.

Obviously, it's not for everyone, but you shouldn't underestimate how easy it is to cover a long distance on a bike--if you're not seriously ill, it is highly likely that you can do a long ride, and that you will surprise yourself. Remember also that you can dose your effort on the bike very easily by going more slowly. At a slow pace, with enough rest stops, and with like-minded and congenial company, this sort of activity is open to a very wide range of people indeed.