Here in the PNW, we ALWAYS have to keep a sharp lookout for debris in the water. The tidal currents create long lines of "drift" where you can find anything from sea foam and kelp, to logs and floating trash. While not as bad as it was years ago since fewer log booms are being towed up and down the Sound to lumber mills, there is still plenty. There is never a leg of any trip here where we don't have to divert around pieces of wood or logs that are large enough to cause potential damage to the prop or rudder.If you decide to go out, keep a SHARP lookout for logs, escaped docks, steel drums, shopping carts, bodies and don't get complacent. I'm not planning on doing any night sailing for a while, either. If you do, have a lantern that someone can use to sweep the water and warn of debris.
So, I'm not sure sure that would keep me from sailing in the Chesapeake, just keep a eye out.