U.S. Route 301 in Maryland in the context of "Eastern Shore of Maryland"

The Gov. William Preston Lane Jr. Memorial Bridge (informally called the Chesapeake Bay Bridge and, locally, the Bay Bridge) is a major dual-span bridge in the U.S. state of Maryland. Spanning the Chesapeake Bay, it connects the state's rural Eastern Shore region with its urban and suburban Western Shore, running between Stevensville and Sandy Point State Park near the capital city of Annapolis. The original span, opened in 1952 and with a length of 4 miles (6.4 km), was the world's longest continuous over-water steel structure. The parallel span was added in 1973. The bridge is named for William Preston Lane Jr., who, as the 52nd Governor of Maryland, launched its construction in the late 1940s after decades of political indecision and public controversy.

The bridge is part of U.S. Route 50 (US 50) and US 301, and serves as a vital link in both routes. As part of cross-country US 50, it connects the Baltimore–Washington Metropolitan Area with Ocean City, Maryland, Rehoboth Beach, Delaware, and other coastal tourist destinations. As part of US 301, it serves as part of an alternative route for Interstate 95 travelers, between northern Delaware and the Washington, D.C., area. The bridge is busy and often congested with traffic, particularly during peak hours and summer months.

Maryland Route 214 (MD 214) is a state highway in the U.S. state of Maryland. Known for most of its length as Central Avenue, the highway runs 24.97 miles (40.19 km) from Southern Avenue and East Capitol Street at the District of Columbia boundary in Capitol Heights east to Beverley Beach. MD 214 connects the central Prince George's County suburbs of Capitol Heights, Seat Pleasant, Largo, and Bowie with the southern Anne Arundel County communities of Davidsonville and Edgewater and several beach villages along the Chesapeake Bay. The highway connects Interstate 95 (I-95)/I-495 (Capital Beltway) to Northwest Stadium, Six Flags America, and several stations of the Washington Metro's Blue and Silver lines, which the route parallels between Capitol Heights and Largo.

MD 214 was constructed as part of three state highways. MD 214 proper was constructed in the mid-1910s from Washington to Largo and extended east to what is now U.S. Route 301 (US 301) through the 1920s. MD 254 was built from MD 2 in Edgewater west to Davidsonville in the early to mid-1920s. MD 253 was constructed from the modern end of the highway southeast to Beverley Beach between the mid-1920s and early 1930s. The gap between Bowie and Davidsonville was filled in the mid-1930s; MD 214 was extended east across a new Patuxent River bridge and took over MD 254's route to Edgewater. In the late 1940s, MD 214 was relocated through Edgewater and extended along most of MD 253 to Beverley Beach. The state highway was widened in Prince George's County in the 1930s and again in the 1950s, and from US 301 to MD 2 in the 1940s and again in the 1950s. MD 214 was expanded to a divided highway at US 301 in the late 1950s, at its interchange with the Capital Beltway in the mid-1960s, and when it bypassed Capitol Heights in the late 1960s. The two-lane gaps between those three segments were filled in the 1980s and 1990s.

Maryland Route 2 (MD 2) is the longest state highway in the U.S. state of Maryland. The 79.24-mile (127.52 km) route runs from Solomons Island in Calvert County north to an intersection with U.S. Route 1 (US 1)/US 40 Truck (North Avenue) in Baltimore. The route runs concurrent with MD 4 through much of Calvert County along a four-lane divided highway known as Solomons Island Road, passing through rural areas as well as the communities of Lusby, Port Republic, Prince Frederick, and Huntingtown. In Sunderland, MD 2 splits from MD 4 and continues north as two-lane undivided Solomons Island Road into Anne Arundel County, still passing through rural areas. Upon reaching Annapolis, the route runs concurrent with US 50/US 301 to the north of the city. Between Annapolis and Baltimore, MD 2 runs along the Governor Ritchie Highway (also known as the Ritchie Highway), a multilane divided highway that heads through suburban areas, passing through Arnold, Severna Park, Pasadena, Glen Burnie, and Brooklyn Park. In Baltimore, the route heads north on city streets and passes through the downtown area of the city.

What became part of MD 2 was originally planned as two different state roads in 1909. The portion between Solomons and Annapolis was built as a gravel road called Solomons Island Road between 1910 and 1915. The portion of road between Annapolis and Glen Burnie was built as part of the Baltimore–Annapolis Boulevard, a road authorized in 1910 to connect Baltimore and Annapolis and was completed in 1924 with the construction of a bridge over the Severn River leading to Annapolis. A state road between Glen Burnie and Baltimore was completed in 1911. MD 2 was designated in 1927 between Solomons and Baltimore, using Solomons Island Road, streets through Annapolis, the Baltimore–Annapolis Boulevard, and the state road between Glen Burnie and Baltimore. MD 2 was marked up to US 1 in Baltimore in 1939. In the 1930s, MD 2 was realigned onto the four-lane Governor Ritchie Highway between Annapolis and Baltimore; the former routing along Baltimore–Annapolis Boulevard became MD 648. Ritchie Highway became a divided highway in 1950. Between the 1930s and the 1950s, several upgrades and realignments occurred to the portion of MD 2 between Solomons and Annapolis. MD 2 was realigned to bypass Annapolis on the US 50 freeway in 1955, with MD 450 replacing the route through Annapolis. The route between Solomons and Sunderland became concurrent with MD 416 in 1960, which was renumbered to MD 4 in 1965. Between the 1960s and the 1980s, MD 2/MD 4 between Solomons and Sunderland was widened into a divided highway, with the bypassed former alignments becoming multiple sections of MD 765. The Ritchie Highway portion of the route was originally the main route between Annapolis and Baltimore until Interstate 97 (I-97) was completed in the 1990s.