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Maryland, the seventh state to be admitted to the U.S. as of March 25, 1788, was one of the thirteen British colonies and was first settled in 1634, when the land which is now St. Mary's County became a refuge for English Catholics. The Calvert family is regarded as Maryland's first family and produced several men with the title of Barons Baltimore. Thanks to lasting effects of the Civil War, Maryland has something of an identity crisis, being a Northern state in some respects and Southern in others. The state's landscape is also varied: from the tall mountains in the western part of the state, to the Piedmont of the middle portion, and the flat coastal plain of the Eastern Shore. The Chesapeake Bay, an important waterway to Maryland's economy, wildlife and recreation industry, separates the rural Shore from the much more populous Baltimore-Washington corridor. Maryland is known for blue crabs and Old Bay seasoning, the beaches of Ocean City and Assateague Island, the U.S. Naval Academy in Annapolis, Camp David, its lacrosse industry, and many additional tourist destinations around the state with varying degrees of prominence.

Baltimore is Maryland's largest city; it contains the Inner Harbor, with such attractions as the National Aquarium and Harborplace; Fort McHenry, the birthplace of "The Star-Spangled Banner"; the stadiums of Major League Baseball's Baltimore Orioles at Camden Yards and the National Football League's Baltimore Ravens; museums such as the Baltimore Museum of Industry and Port Discovery; Druid Hill Park, the home of a renowned zoo; and Pimlico, home of the Preakness Stakes, the middle leg of horse racing's Triple Crown. Despite Baltimore's prominence in the state, the capital is Annapolis, which is filled with history dating back to the colonial era, well before Maryland's statehood. In addition to the Naval Academy, Maryland's State House in Annapolis is a historic property. Maryland's original capital was St. Mary's City, in the same-name county at the confluence of the Potomac River and Chesapeake Bay, where the first English settlers landed. To the southwest of Baltimore and west of Annapolis lie the northern and eastern suburbs of Washington, D.C.; consequently, the corridor in between Baltimore and D.C. is crowded. Maryland has a population of roughly 6.18 million as of the 2020 census.

Other significant cities in Maryland include, clockwise from west, Cumberland, Hagerstown, Frederick, Columbia, Towson, Aberdeen, Chestertown, Cambridge, Salisbury, Lexington Park and Waldorf. Most of these are college towns, military towns, or both.

As far as highways go, Interstate 95 is Maryland's major north-south Interstate route, linking the Baltimore and Washington metropolitan areas over 109 miles. Its children include Interstate 195 to the Baltimore-Washington International Airport, Interstate 395 in Baltimore, the interstate 495 and 695 beltways, and Interstate 895, Baltimore's Harbor Tunnel Thruway. Interstate 70 has its eastern terminus at Baltimore's western city limits and runs 91 miles through Frederick and Hagerstown, and then into Pennsylvania en route to Cove Fort, Utah. Interstate 68 picks up where I-70 leaves off at Hancock and takes drivers further west, ultimately into West Virginia; it roughly follows the course of the old National Road. Interstate 83 runs from Baltimore, through the same-name county and into Pennsylvania's Susquehanna Valley, while Interstate 97, a Baltimore-Annapolis corridor, is one of the country's shortest mainline Interstates, and Interstate 81 forges a quick 12-mile path through the Hagerstown area. Interstate 270 meanwhile links Frederick with the D.C. area, specifically Bethesda.

In U.S. routes, U.S. Route 1 was the original link between D.C. and Baltimore, and on to Philadelphia, Pennsylvania; today it serves mainly as a business route to I-95 between the former two cities and within Baltimore. US 1 gradually turns away from I-95 north of Baltimore as it bypasses Bel Air on a semi-expressway and crosses the Susquehanna River via the Conowingo Dam. U.S. Route 40 is Maryland's longest numbered highway, running 220 miles from west to east across the street and serving several Western Maryland cities as well as Baltimore, then crossing the Susquehanna River on its way into Delaware. U.S. Route 50 connects D.C., Annapolis and takes the Chesapeake Bay Bridge onto the Eastern Shore, where it reaches its end at Ocean City; it also has a separate section of a few miles in Garrett County, in between its West Virginia segments. U.S. Route 29 emerges from D.C. and bisects Columbia before ending at I-70, while U.S. Route 301 serves Southern Maryland and the upper Eastern Shore as a bypass of D.C. and Baltimore. U.S. routes 11, 15, 219 and 220 all have single-county segments out west, the former two serving Hagerstown and Frederick respectively. U.S. routes 13 and 113 serve the lower Shore, with U.S. 13 being the north-south corridor in the Salisbury area. U.S. routes 222 and 522 last a combined six miles within the state.