The Cape Ann dory is a traditional fishing boat, a variant of the beach dory or Swampscott dory. Cape Ann dories were often fitted with a small spirit rig sail, a short folding centerboard, and washboards (bits of deck that run alongside the boat to keep the water out when heeling). The descendants of the Cape Ann dory are still raced as the Town Class. Due to their 'V'-shaped hulls, dories, especially those that are more slab-sided than rounded, have a tendency to heel sharply at first.

Beach dories were designed to be launched behind a breakwater (structure) and into no more than a moderate surf for a day of fishing or lobstering. The oars were generally used to propel the boat to the fishing grounds and the afternoon wind would come up and allow the sails to be used for the return trip.

In 1876, Danish immigrant and fisherman Alfred Johnson sailed a custom twenty foot Cape Ann dory from Gloucester, Massachusetts to Liverpool in 66 days, proving the design built for fishing the rough Atlantic Ocean could handle nearly any weather. Johnson's dory, named the "Centennial" in honor of America's 100th Anniversary, was outfitted with three watertight compartments to prevent sinking if swamped and to hold his supplies. Instead of the simple spirit rig usually found on traditional Cape Ann dories, Johnson equipped his with a square sail and two jibs.

Cape Ann is a rocky cape in northeastern Massachusetts on the Atlantic Ocean. The cape is located approximately 30 miles northeast of Boston and forms the northern edge of Massachusetts Bay. Cape Ann includes the city of Gloucester, and the towns of Essex, Manchester-by-the-Sea, and Rockport.

Cape Ann was first mapped by the explorer John Smith. He had given it the name "Cape Tragabigzanda", after his owner in Constantinople when he was enslaved as a prisoner of war by the Ottoman Empire. She had fallen in love with him. He later escaped in Russia. When Smith presented his map to Charles I he suggested that Charles should feel free to change any of the "barbarous names" (meaning the many Native American names) for "English" ones. The king made many such changes, but only four survive today, one of which is Cape Ann, which Charles named in honor of his mother, Anne of Denmark.

The English colony at Cape Ann was first founded in 1623. It was the fourth colonizing effort in New England after Popham Colony, Plymouth Colony and Nantasket Beach. Two ships of the Dorchester Company brought 32 in number with John Tylly and Thomas Gardner as overseers of a fishing operation and the plantation, respectively. This colony predated Massachusetts Bay charter and colony. For that reason, members of the colony were referred to as "old planters".