You can use Google Maps to find hotels/motels in Williamsburg. Go there and search for "motels near Williamburg, VA". There are also at least three bike shops in Williamsburg. You could ship your bike to one of them for assembly and tuning.
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Absolutely! I'm leaving Hazleton PA on Sunday. When were you planning on leaving?
When you're in the backcountry you need total reliability and easily field-repairable gear.
These would take some research, but could be fine routes - especially the second one, which is on my radar.
But 100 miles a day in March is really difficult because of the limited daylight available.
I would not want to ride an interstate during rush hour in Jacksonville, FL or NYC.