Your memory is very good, Dr. B. Route 1 still does cross the river over the Conowingo Dam. But going that way over the river, or going from Havre de Grace to Perryville / Port Deposit is not crossing the Bay, as all those places are on the west side of the Bay. To get to the Eastern Shore by circumventing the Bay you have to keep going north on Rt. 40-east* to Elkton (formerly the marriage capital of the East Coast, if you remember that) then go east by way of Chesapeake City, where you actually go past the head of the Bay, and fetch up in Chestertown, which is on the Eastern Shore.

* U.S. Rt. 40, which is designated an east-west road, actually runs in the north-south direction from the MD-Del border to Baltimore. This is to confuse out-of-staters who have difficulties when you tell them to go north on 40-east or south on 40-west.