In 1845, he sailed to what became
Portland, Oregon, as the
supercargo (cargo supervisor) of the
Toulon, bringing goods for
Francis Pettygrove's warehouse. he purchased half of
Asa Lovejoy's making up the original claim to the future city for $390 (~$ in ) in cash. Stark bought the land for speculation rather than as a home or commercial property, and so he continued sailing as a merchant and visited the claim only occasionally. Despite often being absent on business, Stark was a civic leader in early Portland. For example, he led the city
Freemasons, membership in which was a status symbol at the time. In 1848, he sailed to
San Francisco to take part in the
California Gold Rush and was a merchant there from 1849 to 1850. In return for giving up the rest of the claim, Lownsdale, Coffin, and Chapman paid Stark for land they had already sold on his acreage, which was roughly and included most of what was then downtown. Later, another dispute between the parties arose after Stark refused to part with two narrow blocks needed to connect the
park blocks. ==Political career==