Ship captains from around the world once sailed into this port, known for its parlors of ill repute, saloons, shanghaiing, and other mid-19th century waterfront shenanigans. In fact, it was developed into two separate urban centers: the waterfront, which catered to hard-drinking sailors and other adventurers, and uptown, on the cliff above the bay, where merchants and permanent residents lived and raised their families away from the riff-raff. The refined Victorian-era women who once shunned Water Street, the main drag through downtown, would likely want to be seen there now. The once rough-and tumble thoroughfare has given way to art galleries and antiques stores, trendy boutiques, coffeehouses, pubs, upscale eateries, and public docks.
Officially settled in 1851, Port Townsend was dubbed the "City of Dreams" because of the early idea that it would become the largest harbor on the West Coast with help from the impending railroad. Instead, the railroad opted for the east side of Puget Sound and the former boomtown experienced a bit of a bust. But the spirit of the town's maritime community and idea that open water lies just off the horizon continues to tinge this place with a certain romance. On a peninsula—the small, crooked arm of the Quimper on the northeastern tip of the larger, torch-shaped Olympic—Port Townsend is a place where the modern meets the Victorian, maritime trades meet the arts, and the sun sets over the water. Its inhabitants are a collection of artists, writers, musicians, mariners, and "shed boys," a term coined in the early 2000s for the mostly single men who live here off the grid. For all of them Port Townsend remains a city of dreams. These knit-cap and Carhartt-wearing residents are well-traveled and highly educated. It's not unusual to find waitresses, bartenders, and students at the boat school who have willingly given up more lucrative positions in larger cities to live here, in the most picturesque gateway to the Olympic Peninsula.