I rode from Charleston, SC to Lambertville, NJ in May, 2010 (
journal here). I faced the same dilemma as you. I was told that if you contacted the bridge, you would be shuttled over if you paid the bridge fee. It seemed best if you made an appointment.
But, after checking out the areas on both sides of the bridge, I decided to skip the Chesapeake Bridge entirely. Instead, I took 2 ferries to get across the Bay. First, I took one from Reedville to Tangiers Island to Crisfield, MD and the Delmarva Peninsula. The second one was from Lewes, DE to Cape May, NJ. Note that I was riding in the opposite direction that you are planning.
The above referenced journal has links to detailed planning information about this trip that might help you.
Between the Outer Banks and Reedville, I rode to and spent a couple days seeing Williamsburg, VA and other historic areas that I highly recommend.
You can read about
my ride starting at the Outer Banks and points north, if you like, though after Sandy, the Outer Banks will likely look much different.
While I can't say that this was my favorite bike tour, I'd never spent much time on the Atlantic Coast and I now have a much better sense of it. Also, Williamsburg was fabulous.