It has existed since at least 1761, which is when a milestone was placed on the street, on the order of Benjamin Franklin, due to its being on the King's Highway, to denote its distance from Boston, Massachusetts.

Many are located in the Gilman Road and Pleasant Street areas, which leads to the possibility of it being a future historic district.

Several people pertinent to the shipbuilding industry lived on Pleasant Street, including Captain William Gooding.

Pleasant Street was also part of the northern extension of the King's Highway that ran between Charleston, South Carolina and Boston, Massachusetts, laid out between 1650 and 1735.

[3][4] Trolley cars of the Portland and Yarmouth Electric Railway used to run, every fifteen minutes, from Portland, through Falmouth Foreside, up and down Pleasant Street and onto Main Street between 1898 and 1933,[5][6] when the advent of the automobile made rail travel a less convenient option.

A shed for passengers awaiting the trolley cars stood at the southern end of the street.

[9][11] Several notable members of Yarmouth's seafaring past have lived in the brick number 51, which was built in 1831: mariner Enos Chandler, master shipwright Lyman Fessenden Walker and Giles Loring.

[9] The cape at number 125 is a well-preserved, high-style Greek Revival with details including an entry surround with a tablet and sidelights.

[9] At the apex of the Pleasant Street corner is Gooding's End, named for the family involved in shipbuilding down at the harbor.