DO. SEE. EAT. DRINK.

DO. SEE. EAT. DRINK.

#016: PORTLAND

For Lovers of Independent Culture

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DO. SEE. EAT. DRINK.
Jun 05, 2026
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Photo: Mono-Space High Fidelity Listening Gallery

Portland may be America’s best city for spending an entire day following your curiosity. A bookstore that is also a gallery. A gallery also has a coffee shop. A coffee shop in a park built on an extinct volcano. Somewhere along the way, you’ll eat one of the best meals you’ve had all year and wonder why more cities don’t work like this.

What I love most about Portland is that so much of what makes it special still feels relatively unpretentious. The city has world-class restaurants, ambitious contemporary art spaces, and one of the country’s great bookstores, but it rarely feels interested in advertising any of it too loudly. Much of Portland’s charm lives in the spaces between destinations.

More than most cities, Portland rewards wandering. Pick a neighborhood, start walking, and see what happens. Alberta Arts District, Mississippi Avenue, and Division Street are all particularly good places to spend a day without much of a plan.

Portland Aerial Tram | Photo: Go By Tram

Ride the Tram. One of my favorite inexpensive activities is taking the aerial tram up to Oregon Health & Science University. On a clear day, you can see Mount Hood, Mount St. Helens, and much of the city spread out below. It’s also a reminder of how closely Portland’s urban life remains tied to the surrounding landscape.

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