The chances of finding a roof is less then zero. Some towns still have lists of people who will take in bikers. It helps if you have a profession, puts the person letting you in at ease. It sounds as if you are carring your supplies and not having someone take it to the next town. Try to hook up with a group to haul your "stuff". Plan on washing y our clothes in a giant zip lock bag , then you can take less clothes
( unless you find someoneto haul your stuff} Talk to a local bike club
good luck
If it is not too obvious, the most helpful tip I have that I learned from my recent solo and unsupported 375-mile trek to St. Paul is to have gear stowed low down on both front and rear wheels. Otherwise the steering is dangerous and the bike unstable especially on descents. Front racks are not expensive. Also be sure to have a first aid kit with gauze, alcohol wipes, first aid cream, insect repellent. You should have a can of dog spray readily accessible. Lights are essential even if you think you will not ride beyond daylight hours - you never know. And yes washing quick-dry clothes in Woolite saves taking too many. And, of course, take the saddle you have the most affection for.
For long stretches, sunflower seeds break up the miles. Cranberries and walnuts are good snacks while riding. Have a bag up front or one of the bags time trialists use on their stem.
i tub vaseline, mix in one large tube boil cream and one large tube neosporin. mix liberally and apply generously. if your saddle isnt shiny after a few hours of riding you didnt apply enough.
Jon said:
Pack your clothes in ziplocks and buy some DZ Nuts. My taint chaifed like a mofo.