The original span of the Chesapeake Bay Bridge was built in 1952, replacing the old ferry which used to connect Anne Arundel county to Kent Island. The second span opened in 1973. (http://www.roadstothefuture.com/Chesa_Bay_Bridge_History.html) Since the 1950s, tourism on the Eastern Shore has boomed, but mainly in association with its link to Ocean City, Rehoboth Beach, and points between. Salisbury, Cambridge, and Easton are now growing as the acceptable commuting distance to Annapolis and Baltimore has grown. I work in Annapolis, and with lots of folks who live in Queen Anne's County.
Another effect of the Bridge was to kill the small vacation spots (and their eateries) on the Western Shore of the Bay. These were, in the late 19th to early 20th century, connected to Baltimore and Washington (and to each other) by a system of steamboats.
Chesapeake Beach (http://www.baygateways.net/general.cfm?id=81) is a good example. (Their own website is inaccessible.) Otto Mears' Washington and Chesapeake Railway Company ran from the fall of 1898 until the spring of 1935. The Depression mostly killed the resort itself, and automobiles meant people could travel to other locales more easily. But Chesapeake Beach itself had a revival in the late 1940s/50s as a gambling casino resort. The construction of the bridge, coupled with the banning of slot machines in 1967, spelled the death of Chesapeake Beach and other resort towns on the Western Shore. These towns became small rural market towns, catering mostly to local crowds. As did their restaurants.
U.S. Route 301 (a Blue Star Memorial Highway) is another once-great route for roadfood. Before I-95 was constructed, U.S. 301 was jammed with motels, casinos, and restaurants. Now they're mostly overgrown, or converted to other uses. Wigwam Walls Bakery (now more politically correct "Walls Bakery") in Waldorf is a good example of adaptive re-use (http://www.agilitynut.com/wigwams5.html).
Besides commuting distance and subsequent suburban sprawl, the advent of the automobile and the Bay Bridge construction, and that of I-95, the other two major factors affecting life (and restaurants) in Southern Maryland has been the military and the oyster harvest. When Patuxent River Naval Air Station opened in the early 1940s, the economics of St. Mary's County changed abruptly. Bars and eateries catering to the huge influx of new people, both military and civilian, sprang up in the new town of Lexington Park as well as at various crossroads throughout the County. These establishments typically had great access to fresh seafood from the St. Mary's County watermen, who plied the western Bay and the Potomac for oysters and other shellfish and fish. I went to college at St. Mary's College of Maryland, and can tell you that by the late 20th century, most of these restaurants were struggling to compete with large chain restaurants. So their prices tended to rise, while the largely fried quality of their food . . . well, didn't really. This may have changed, but . . . I kinda doubt it. In 1987, the only restaurant in the county which was open after 10pm was Subway. By 1991, there were several Asian restaurants, an IHOP, and a Perkins, most of which were constantly packed with military personnel, contractors, and students. Look at the place now:
http://www.co.saint-marys.md.us/Tourism/Restaurant/lexparkrestaurants.asp Egad. There's even an Applebees.

At the bottom of the page is The Roost. Apparently this was the bar with the kooky decor featured in The Right Stuff.
The oyster harvest, however, has put a major crimp in the seafood industry in the county.
http://www.washingtonpost.com/wp-dyn/articles/A43629-2004Nov11.html quote: For decades, the Browns, like most watermen, have adapted as diseases, pollution and commercial fisheries have taken their toll on the Chesapeake Bay and its rivers. Oysters, an important filter for the water and once the mainstay of the region's fishing industry, have been decimated, their numbers dropping to historic lows.
In the 1970s and '80s, before diseases started their rampant spread through the bay, the average harvest reported to the Maryland Department of Natural Resources was more than 2 million bushels. This year, DNR officials expect about 15,000. Just a few years ago, there were thousands of people oystering in Maryland; this year, they expect fewer than 150.
In 1987, the Virginia Marine Resources Commission issued more than 2,000 licenses for oystering; in 2003, it issued about 300. And on the Potomac -- famous for its Oyster Wars five or six decades ago, when shots were fired over fishing rights and fast boats slipped past the authorities at night -- little or no harvest is anticipated this year.
The local restaurants down there now appear to be forced to import their catch of the day from the Gulf of Mexico. I don't know if this has raised prices or decreased quality, because I haven't been down there in a while. However, about four years ago my daughter (then 18 months) and I had crab cakes at Nook and Monks restaurant/theatre/coffee house in Leonardtown. She's loved them ever since.