The Eastern Promenade Trail terminates in the Old Port and connects to the East End Beach.

Portland's Post Office, designed by Alfred B. Mullett, stood at the location from 1871 to 1965,[4] when it was demolished and replaced by a parking lot.

[8] A prominent feature of the park was a trompe l'oeil mural painted on the gable end of 80 Exchange Street.

It was removed during building restoration work in 2018, and was repainted to a design by South Portland artist Will Sears.

At the outbreak of the American Revolutionary War, a large part of the city was destroyed by fire in a British raid in October 1775.

At the top of Exchange Street, strategically located across Congress Street from Portland City Hall, is the Press Herald Building built in 1923 and expanded in 1948 as the headquarters of the Portland Press Herald.

[19] The Old Port was transformed in the 1970s when real estate developers purchased derelict buildings and refurbished them into apartments, condos, offices and retail space.

[20] During that same decade, the Old Port Association formed and helped halt the city's demolition of historic buildings (see Union Station) and lobbied for street scape improvements.

For the first 36 years (1973–2009), it took place on the first Sunday in June; however, noting weather patterns which consistently brought rain storms on that day, organizers moved the festival to the second Sunday in June 2010, avoiding heavy rain.

[24] In June 2019, the final Old Port Festival occurred, though some area business owners sought to continue the event.