[5] Milwaukie was settled in 1847 and formally platted in 1849 as a rival to the upriver Oregon City by Lot Whitcomb, who named it for Milwaukee, Wisconsin.

[6] Some accounts also state that the Oregon city used an alternate spelling to prevent confusion at the post office.

[7] Whitcomb arrived in Oregon in 1848 and settled on a donation land claim, where he built a sawmill and a gristmill.

[11] In 2009 new apartments and retail space were under construction in the downtown area of Milwaukie, and a riverfront park was being developed.

Dark Horse is known for publishing works including Sin City, the character Hellboy, and the original graphic novel series 300, as well for producing dozens of films and television series, including The Mask and Timecop, based on characters created by Dark Horse founder Mike Richardson.

The total office space of Dark Horse Comics occupies three city blocks in downtown Milwaukie, sporting numerous display windows visible to transit riders.

[23] A big draw to the city was noticed right after the Orange Line from TriMet, a $1.4 billion project connecting the close-in suburb right to the heart of downtown Portland, finished in 2015.

A year after the opening of the Orange Line, housing prices had risen 12.2% and city officials said there were no vacancies for retail storefronts in Milwaukie's downtown area.

[24] In addition to the new Orange Line, Milwaukie finished a $2.2 million project to the city's waterfront park.

Since 1996, Milwaukie High School has annually hosted the nationally recognized[26] Living History Day.

Since 2010, the bus stops that previously comprised Milwaukie TC are no longer designated as a "transit center" by TriMet.

In fall 2015, the focal point for rider transfers between routes shifted southward from the former transit-center location, with the opening of a new light rail station at the south end of downtown.

[35] The 7.3-mile (11.7 km) line was sufficiently complete by May 15, 2015, for 500 passengers to make an initial special run along its whole length.

[31] Streetcars began serving Milwaukie in August 1892, when the East Side Railway extended its service beyond the then-town of Sellwood.

[37] The company built a carbarn and workshop in downtown Milwaukie, on Jackson Street at River Road (now McLoughlin Blvd.

[39] Oregon Motor Stages, Inc., had provided some bus service through Milwaukie until 1954, when it abruptly ceased all operation.

The service, which ran twice a day in each direction and connected Portland with Eugene, was introduced on a trial basis in August 1980 and discontinued at the end of 1981.

Current mayor Lisa Batey took office on January 1, 2023, after winning the November 2022 election against Kathy Hyzy.