Old Town, the oldest commercial district in Portland, holds the blocks where the city was founded and where its most complicated history unfolded, and you are in the middle of them. Old Town grew up along the Willamette waterfront in the 1850s and 60s, built on land that was flood-prone but strategically valuable for river commerce. The cast-iron facades on many of these buildings date to the 1880s and 90s, when Portland was one of the fastest-growing cities on the West Coast.
Beneath the streets, according to local legend, runs a network of tunnels through which sailors, loggers, and drifters were supposedly drugged and sold to ship captains who needed crew — a practice called Shanghaiing. The historical evidence for the extent of this trade is disputed, but the tunnels are real and can be toured, and the social conditions that made such exploitation plausible were very real. Old Town has functioned as Portland's entry point for successive waves of immigrants, including the Chinese workers who built the railroads and settled here beginning in the 1870s.
Today Old Town is the center of Portland's social services infrastructure, home to the largest concentration of homeless services in Oregon. The neighborhood holds Portland's most layered history in its least genteel blocks.