48 Hours In Portland, Oregon

Above (clockwise): The Keen Garage, Food cart block, Columbia River Gorge, and the Portlandia sculpture

Quirky and slightly peculiar, in the most charming of ways. Thanks to the show Portlandia, this is the impression many of us have of this west coast city and after a quick visit, we’d have to say we found much of this to be true. It is home, for example, to both one of the smallest parks around (that’s offers enough space for about one person to stand) and vegan strip clubs. But it also boasts fantastic food, gorgeous nature hikes and friendly folks–you won’t be hard pressed for fill your time on a weekend getaway.


For quick trip, you’ll want to be centrally located and the Hotel Monaco is downtown, making walking to the Pearl District, the food carts and Pioneer Square easy. If you like to fit in a run while you travel, you’re by the riverfront, too. Both the lobby and the rooms feature an eclectic look of a mix of prints and textures, almost making you feel as though you’re staying at your eccentric relative’s home rather than a hotel. Psst: there’s complimentary wine daily in the lobby from 5 to 6 p.m.


As the world headquarters for hiking boot company KEEN, stopping into its stunning flagship store, the Keen Garage, is a must in Portland. Located in a refurbished 1907 building, the store and head office feature original flooring and elements such as tables made of bowling alley floors since the mandate was to take as little as possible to the dump from the renovation (grand dumpster total: one!). The 4,000-sq- ft store (known as “the garage,” because that’s where you keep your most prized possessions, according to KEEN owner, Rory Fuerst) boasts the entire KEEN lineup of products (and you will have to gear up for your hiking in Portland, after all) with the shoes displayed on shelves that you can rotate like a conveyor belt.

If you’re a booklover (or just trying to get featured  the @hotdudesreading Instagram feed) then a must-visit is Powell’s City of Books. The famous bookstore (which claims to be the world’s largest indie bookstore for used and new books) is heaven for those who love the printed word. Enter the landmark, which has since been expanded and covers an entire city block, and grab a map to help you find what you’re looking for (or you can happily stumble through the stacks). Besides books, there are plenty of lifestyle goods to peruse as well, from mugs and temporary tattoos to stationery and tote bags.


Tacos are always a good idea, and that’s especially the case at Santeria. With retro pop and hip hop playing and religious candles on the table, this casual spot is perfect for a late-night bite and a margarita. You can order your taco protein and toppings exactly how you’d like it, or if that’s too much for you to decide on, just order the taco flight, which features the resto’s three faves (tinga, al pastor and cochinita) with rice, beans and guac.

Every foodie will start contemplating moving to Portland after experiencing its food cart scene. The Alder pod downtown is one of the largest pods of street-food carts and you can easily get overwhelmed by the variety available. Some of the most popular include Nong’s Khao Man Gai (known for its ginger chicken and rice), The Whole Bowl (vegetarian bowls, if you’re so inclined) and the Grilled Cheese Grill. Pick up your affordable lunch and chow down while standing around with the locals.

Voodoo Doughnuts get much of the attention in Portland when it comes to this sweet treat (and you can expect long lineups of tourists) but for a gourmet take, Blue Star Doughnuts is the one we favoured. Avoid going at the end of the day, as you might find they’ve sold out and closed early. Delectable doughnuts choices include ones such as blackberry compote-filled doughnuts dusted with an out-of-this-world peanut butter powder, and a rich Valrhona chocolate crunch.


Blink and you may miss Mill Ends Park entirely. There won’t be any musics festivals held in this park. Billed as the “world’s smallest park,” the circular park measures about three feet across and is located in the median of SW Naito Parkway. Mill Ends Park is typically filled with flowers and a small shrub so while you can’t stand in the park, you can stand beside the curious space established by journalist Dick Fagan in the late 1940s.

For a taste of Mother Nature on a much larger scale than Mill Ends Park, grab the hiking boots you got at the Keen garage and drive about an hour from Portland to the Columbia River Gorge. Here, you can put those boots to the test on one of the many day hike trails (there’s everything from trails for beginners to advanced). Whichever hike you take, do not miss stopping at the stunning cascade of water of the 600-plus feet of Multnomah Falls, which according to Native American lore was created to woo a princess who wanted a private spot to bathe.

Tags: Oregon, Travel Guide

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