If Portland’s Old Town/Chinatown District were a person, it would stay out too late, sleep in past noon and not always feel like shaving before leaving the house. Portland’s Old Town/Chinatown has a slacker’s charm and an enduring grittiness that people either enjoy or avoid.
I worked in Old Town for 18 years. It has my favorite pizza restaurant, a terrific drag show, a great place to see a rock concert, and is where I park to take my waterfront walk across the Steel Bridge over to the Eastbank Esplanade.
For visitors, it has the city’s most intriguing history, a gorgeous Chinese Garden, two arts and crafts markets, streets closed to aid and abet bar hoppers, and a new food hall that lives up to Portland’s lofty culinary standards.
The Skidmore/Old Town Historic District was Portland’s first recognized historic district. It has exceptional architecture, including one of the finest collections of cast-iron buildings in the nation. It’s also known where Portland’s pioneer merchant-entrepreneurs transformed the city from a stump-strewn clearing to the cultural, financial, trade and transportation hub of the Pacific Northwest. The Chinese and Japanese were among many immigrants who found work and refuge in the area.
Old Town/Chinatown offered important social services for the working classes and various ethnic and social groups. This includes lodging for itinerant workers, sailors, and loggers; union halls; reading rooms; missions and chapels; and ethnic publishing houses. It also was renowned for its saloons, gambling halls, burlesque houses and brothels.
Japanese, Spanish, Korean, American, coffee and juice bars populate the new Pine Street Market. Opened in 2016, the former livery and horse-drawn carriage storage building has been transformed into a bustling, open food hall serving plates to please any picky palate.
Old Town Pizza not only has some of the city’s finest brick-oven pies, it has the funkiest decor (think of eating pizza on grandma’s old furniture). It’s also reputed to be haunted. Plus, a tunnel that once led to a river lies underneath. It was rumored that sailors were shanghaied to ships in waiting. If these stories intrigue you, sign up for walking tour of Portland to learn more about the Rose City.
Lan Su Chinese Garden sits like an urban oasis. Enter and stroll along covered walkways, bridges, open colonnades, pavilions and a richly planted landscape. A visit to the garden helps you delve deeper into the history and culture of China. Lan Su Chinese Garden’s living collections offer hundreds of native Chinese plant species and forms.
Get a salty taste of Portland’s history at Dan and Louis Oyster Bar — the oldest family-owned restaurant in town. Since Louis C. Wachsmuth opened the doors in 1907, five generations have been involved in bringing seafood to Portland diners. It’s well-known for oyster stew, steamer clams, seafood entrees and platters of fresh oysters. Oyster varieties change daily.
If it’s the weekend, walk a block to the outdoor Saturday Market and neighboring Skidmore Market near the historic Skidmore Fountain. Buy a handcrafted souvenir, get your fortune told or gnaw on an elephant ear.
Enjoy a nostalgic trip back to your childhood at the Ground Kontrol arcade. Not only does it have more than 60 classic video games and pinball machines, it has a full bar and DJ after 5 p.m.
Bellies full, you’re ready for the hilarious show at Darcelle’s, which kicks out Las Vegas-style cabaret revues of glitz, glamour and comedy. Around the corner is one of the city’s best dance clubs, CC Slaughters. Another option is the Dixie Tavern, a crowded bar known as “Portland’s rock and roll tavern.” It has scantily clad dancing bartenders and an inflatable sheep behind the bar. Let your imagination run wild with that one, cowboy.
Speaking of scantily clad, the Silverado gay bar down the street doubles as a male strip club. Its atmosphere is sometimes pierced by the screams of bachelorette parties congregating for the hot dog show.
Still hungry? Get in line for a naughty-shaped pastry at VooDoo Doughnuts down the street. It’s open 24/7.
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