I rode through Chester in 1983 and I still remember the absolutely beautiful life guard at the pool. I was in my late teens and camped out near the pool.
As far as an ideal host town, well I enjoy free/low cost hiker/biker only bunk houses which is typically a donated house converted into a no-frills dorm style house with bunk beds, kitchen, etc. Due to the summer heat, it would probably need to have AC or at least heavily shaded with lots of ceiling fans.
If you can't do that do to possible vandalism/cost, having a "campground" with large tent pads that are level; slightly raised (1 RR tie); semi-loose dirt (think vegetable cargen, not cement or gravel) to get tent stakes in; a few picnic tables; water faucet; bath house (hot water nice); pay washer/dryer in town; pay phone close by; electrical outlets (to charge cell phones), clothes line, and a "hitchin post" for the bikes. I would like for it to be in walking distance to the library (internet), and/or wireless service. All in the shade and so where car lights don't keep you up at night.
If lighted, have the lights either switched by the user or turn off 30 minutes after dark.
All for an honor system (put mone in box) low cost system.
I have tried for years to get ACA to consider working with town along the route to develop stopover towns like the above with no success :|.
As a person with a background in tourism destination development, I (as a town) would gladly spend the relatively small amount of money for the tax base and economic benefits. It would pay for itself in a few years and help the local businesses.
Since Chester has/had a pool, the biggest expense is already taken care of (bath facilities and phone).
Hope you do it. Best of luck and whatever happened to that blonde?!?
Happy trails and may the wind be at your back!