Steve M from Festus MO on 9/10/2010 5:40:48 PM:
A lot of people have done the full trail, it's a great ride and a somewhat popular thing to do - the biggest factor will be your own physical condition and willingness to push on.
A couple of friends and I did the trail from Clinton to St Charles over a weekend. We rode from Clinton to Jeff City the first day, then Jeff to St Charles the second day. We were not in the best of shape at that point in the season (June), but met our goal. Not that it matters too much, but we are in our 40s and 50s.
In general, the trail will be in good enough shape for a trailer, but heavy rains can cause problems. There are trail condition updates available at this site to keep you abreast of the situation.
I would say that as long as you are in decent cycling condition, 3 days out and 3 days back wouldn't be a big problem. (roughly 80 miles per day).
My 2 cents,
SteveM