Old Town’s Ankeny Alley

Portland's nightlife takes to the streets in a pedestrian-only stretch of the city's Old Town district.

Old Town/Chinatown’s Ankeny AlleyOld Town/Chinatown's Ankeny Alley at night

Portlanders love the outdoors — so much so that even when they’re enjoying inside activities, they’re much happier doing them outside. For example, on a one-block stretch of Southwest Ankeny Street between Second and Third avenues in Old Town, picnic tables trump pick-up trucks, since the cobblestone alley has been closed to traffic. Instead, under a lattice of white twinkle lights, revelers enjoy cocktails, dinner and, perhaps most of all, doughnuts.

Closed off in 2011 as a pilot program between the street’s businesses and the city, the space stayed car-free, ushering in a new wave of al fresco business across the city, where restaurants and bars can rent parking spots in front of their establishment and install seating in place of cars. But here, the local businesses have banded together to keep the street traffic-free, indefinitely and year-round.

The on-street eats stem back to more than 100 years ago when the founder of Dan & Louis Oyster Bar peddled live crabs on these very sidewalks. Today the popular seafood eatery serves their fresh seafood curbside, cooked to perfection. Next door, the nightlife crowd at art-infused Valentine’s spills out of the tiny lounge, able to sip the night air while still enjoying the live music and DJs making melodies inside.

Further up the block, a pair of eateries tickle the taste buds and offer outdoor seating at which to enjoy the festive atmosphere. Voodoo Doughnut, open 24 hours a day, has painted their picnic tables pastel colors to match their rainbow of candy-coated confections (and their bright pink boxes).

To be sure, the alley is pure Portland, and its newest resident, the Know Your City information kiosk is dedicated to keeping it that way. The kiosk offers history tours, lectures, publications and programs dedicated to showing off Portland — and what better place than in the thick of the city?

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