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Curated by Our Guild Explorers · Updated August 2026
The Old Line State · Capital: Annapolis · The Northeast
Chesapeake blue crabs, sailing history and the wild ponies of Assateague.
What makes Maryland worth the trip.
Sailing, seafood and waterfront towns.
The Bay's signature feast, hammer and all.
Annapolis, the Naval Academy and colonial ports.
The capital and the places worth building a trip around. Click a marker for a quick note and hotels.
Long before Europeans arrived, the Chesapeake Bay watershed was home to Piscataway, Nanticoke and Susquehannock peoples who fished its rich waters and farmed its shores. English settlers established the colony in 1634 under a charter granted to the Calvert family, naming it for Henrietta Maria, queen consort to Charles I, and founding St. Mary's City as an early experiment in religious toleration for Catholics and Protestants alike.
Maryland became the seventh state to ratify the Constitution in 1788 and later donated land carved from its own territory to create the new federal capital, Washington, D.C. During the War of 1812, the bombardment of Fort McHenry in Baltimore harbour inspired Francis Scott Key to write what became 'The Star-Spangled Banner,' and the state's divided loyalties during the Civil War left a complicated legacy still visible in its historic sites.
Today Maryland blends old maritime culture with modern industry: Annapolis remains a working sailing capital and home to the U.S. Naval Academy, Baltimore has reinvented its harbourfront around biotech, arts and its storied seafood scene, and the Eastern Shore's marshes and barrier islands preserve a slower, tidewater way of life that has defined the Bay for centuries.
The Star-Spangled Banner was written by Francis Scott Key in 1814 while watching the British bombard Fort McHenry in Baltimore Harbor, and that flag now hangs in the Smithsonian.
The signature places to build a trip around.
Sailing capital and home of the U.S. Naval Academy.
Selected hotels
The Inner Harbor, aquarium and Fort McHenry.
Selected hotels
Wild ponies on a windswept barrier island.
Selected hotels
A lively Atlantic boardwalk resort.
Selected hotels
Skip the tourist crab houses downtown and head to a place like the ones in Annapolis or along the Eastern Shore where they steam crabs by the bushel, and go in late summer when Maryland blue crabs are at their heaviest.
Late spring through autumn; crab season peaks in summer.
Cold and often grey, with occasional snow; a quiet time to explore Baltimore's museums indoors.
Blossoms and mild temperatures make Annapolis and Washington-adjacent day trips a pleasure.
Peak crab season and beach weather at Ocean City and Assateague, though hot and humid.
Crisp air, fewer crowds and colourful drives through rural Maryland countryside.
Annapolis is the capital of Maryland.
Baltimore is the largest city in Maryland.
Maryland became the 7th U.S. state on April 28, 1788.
Maryland is known for chesapeake blue crabs, sailing history and the wild ponies of Assateague.
Late spring through autumn; crab season peaks in summer.
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