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Portland was named by a coin toss in 1845. Francis Pettygrove of Portland, Maine won the flip against Asa Lovejoy of Boston, Massachusetts, and the city got its name from a small town that has been quietly pleased about it ever since. The city grew as a Pacific Northwest timber and shipping port, rough and rowdy through the late 19th century with a reputation for saloons and bordellos and the practice of shanghaiing sailors for outbound ships. The Crystal Ballroom on West Burnside, built in 1914 and still operating, was the dance hall where the counterculture of the 1960s took hold in Portland, and the psychedelic scene it hosted had continuity with the punk and indie music scenes that followed decades later.

Powell's Books on West Burnside occupies a full city block and holds around a million new and used books organised by subject across multiple coloured rooms.

It has been at its current location since 1979 and remains the largest independent bookstore in the United States. Portland has more breweries per capita than any other American city, a distinction it takes seriously, with taprooms spread from the Pearl District to Southeast Hawthorne to the Alberta Arts District in Northeast Portland. Forest Park, a 5,200-acre urban forest with 80 miles of trails beginning just northwest of the city centre, is one of the largest urban parks in the United States.