The Pride was originally built as an authentic reproduction of a 19th century Baltimore Clipper schooner, patterned after and named for the legendary Baltimore built topsail schooner Chasseur sailed by the privateer Thomas Boyle. The Chasseur was known as the "Pride of Baltimore" and participated in the War of 1812.

One of the most famous of the American privateers, Captain Thomas Boyle sailed his Baltimore clipper, Chasseur, out of Fells Point, where she had been launched from Thomas Kemp's shipyard in 1812. On his first voyage as master of Chasseur in 1814, Boyle sailed east to the British Isles, where he harassed the British merchant fleet and sent a notice to George III, by way of a captured merchant vessel, declaring that the entire British Isles were under naval blockade by Chasseur alone! Despite its implausibility, this caused the British Admiralty to call vessels home from the American war to guard merchant ships sailing in convoys. Chasseur captured or sank 17 vessels before returning home to Baltimore on March 25, 1815, where the Niles Weekly Register dubbed the ship, her captain, and crew the "pride of Baltimore" for their achievement.

In 1975, the City of Baltimore, as part of a plan to revitalize its Inner Harbor, proposed the construction of a replica sailing vessel as a centerpiece, posting a notice requesting proposals for "an authentic example of an historic Baltimore Clipper" to be designed and built using "construction materials, methods, tools, and procedures are to be typical of the period."

A design by Thomas Gillmer was chosen, and master shipwright Melbourne Smith oversaw the construction of the vessel next to the Maryland Science Center in downtown Baltimore where residents and curious visitors could watch the craftsmen working with tools and techniques of two centuries earlier. Congresswoman Barbara Mikulski performed the launching ceremonies on February 27, 1977, only 10 months after the start of construction, and the Pride of Baltimore was commissioned on behalf of the citizens of Baltimore and Maryland by the Mayor William Donald Schaefer two months later on May 1, 1977.

The Pride sailed over 150,000 nautical miles (2.8×10⁵ km) during her nine years of service, visiting ports along the Eastern Seaboard from Newfoundland to the Florida Keys, the Great Lakes, the Caribbean and the West Coast from Mexico to British Columbia. She visited European ports across the Atlantic in the North Sea, the Baltic Sea and the Mediterranean.

On May 14, 1986, returning from Britain on the trade route to the Caribbean, the Pride was struck with what the US Coast Guard later described as a microburst squall (see also: White squall) 250 nautical miles (463 km) north of Puerto Rico. The vessel was hit with 80-nautical-mile (148 km) hour winds, capsizing and sinking her. Her Captain and 3 crew were lost, and the remaining 8 crewmembers floated in a partially-inflated life-raft for four days and seven hours with little food or water until they were rescued by the Norwegian tanker Toro.

The Pride's lost captain and crewmembers (Armin Elsaesser 42, Captain; Vincent Lazarro, 27, Engineer; Barry Duckworth, 29, Carpenter; and Nina Schack, 23, Seaman) are remembered to this day with a memorial on Rash Field in Baltimore's Inner Harbor.

The Pride of Baltimore II is an American sailing ship owned by the citizens of the state of Maryland, and operated by Pride, inc., a private, non-profit organization. She was launched in 1988 after the loss of the first Pride of Baltimore, and continues the role of Maryland's Flagship and Goodwill Ambassador, promoting business and tourism in Maryland.

Unlike the original Pride, the Pride II is not a replica of any specific vessel, and though it represents a type of vessel known as a Baltimore Clipper, it was built to contemporary standards for seaworthiness and comfort. Pride II, like its predecessor, is a topsail schooner, with two large gaff sails (one on a boom and one loose-footed), a main gaff topsail, several headsails, and a square topsail and flying topgallant on the foremast. She also flies studding sails (stun's'ls), rare on modern traditional sailing vessels. These additional sails are set along the edge of the square topsail and the mainsail, supported by additional spars known as stun's'l booms.