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Portland Offers A Happy Home for Hipsters


Oregon’s culinary capital is one of America’s youngest cities and on my first visit I couldn’t help but gawk at the parade of sexy tattooed bartenders, waitresses, taxi drivers, bellmen and donut factory pastry chefs who seemed to own the streets. It was clear, Portland offers a happy home for hipsters.

For a Toronto point of reference, my four days here felt as though West Queen West had just decided to plant itself on the West Coast and call itself a city. My attraction to the place and its people was abnormally severe. Whether sitting on my own sipping a cocktail at a speakeasy or hiking through a national park en route to a roaring waterfall, I was constantly reminded I was single and ready to mingle. My lord, the number of times I awkwardly fidgeted with my sunglasses and tossed my long blond locks. Be still my heart!

There is no better place in Portland to tap into the cities unique hipster vibrations than at The Jupiter Hotel. The 80 room property located in South East Portland on Burnside was originally a mid-century motor inn and has recently been renovated and reimagined as a funky boutique hotel. Upon arrival I was immediately reminded of Toronto’s famed Drake Hotel as the property celebrates quirky artistic aesthetic in an edgy way. The hotel’s lobby is “a little bit alfresco,” offering a tented canopy where sparkling chandeliers glow at night. In the morning guests can be found sipping their morning coffee on pretty white furniture, surrounded by a fern and bamboo forest which offers a nice dash of calm-me-down-zen. Rooms at The Jupiter are crisp meets minimalist with complimentary coffee from local roaster Water Avenue, free wifi, city bikes for rent, eco-friendly Natura bath products and friendly front desk concierge service. Spotting a hotel branded complimentary condom on my bedside table? The cherry on my sundae!

One night after a particularly adventurous day I dabbed my lobster tan with a napkin while sipping an iced cold bottle of beer from Rogue brewery. Twinkling lights shot from the chandelier above, creating the perfect nook to people watch…

Directly across from the hotels lobby sits the Doug Fir Lounge, a local hub for hipsters with a penchant for greasy spoon eats, craft beer, creative cocktails and live music rock n rollers. The interior is a total gong show, timber lodge meets spaceship modernity. Upstairs couples slug through frothy pints and burgers while downstairs live music junkies bob up and down with a folk band. The place is full of ironic tattoos (a young woman in dreadlocks drinking a tall can has a pink princess etched onto her right shoulder) while burly men scratch their beards as if wooing me over. I’m most thrilled to notice I’m not the only gent in here sporting a man bun… could this be Home Sweet Home? Out back a cool crowd of skater-boy Prince Charming’s tell personal stories about their recent skinny dipping adventures around a cozy, crackling campfire.

The Greater Portland Region offers a multitude of exciting experiences for happy-go-lucky hipsters. Enjoy outdoor hiking adventures and sud-sloshed beer tour in Mt Hood Territory; forest canopy zip-lining and sake sips in Washington County; tranquil Chinese Garden and jaw dropping Whiskey Library in the heart of the city.

Sips and Nibbles: Portland is a food lovers paradise, and in less than four days I seemed to eat up most of it. Head to Le Pigeon for pretty on your plate, Bob’s Red Mill for a grain-centric brunch, the cheap and cheerful Country Store for beer growler and BBQ, Noble Rot for a fresh salad plucked from the chefs rooftop garden, Pepe Le Moko for moody speakeasy vibes, Clyde Common for a decadent dinner and top notch people watching opportunities, Voodoo Doughnut for the cities most famous sweet treat, Produce Row Cafe for a leisurely sip and snack, Oso Market + Bar for top notch vino and petite sharing plates, Katchka’s taste of Russia and the jaw dropping Multnomah Whiskey Library.

Beer Break at Breakside Brewery: Breakside Brewery opened its new taproom and brewery January 2013 with 24 taps and lots of big flavour. After just three years in its production facility in Portland, Breakside debuted a new 7,000 sq ft brewery, upping its production to 5,000 barrels (with plans to double that soon). Brewmaster Ben Edmunds and his team brew about 100 imaginative beers each year, from solid staples to experimentals with ingredients ranging from beets to Muscovy duck. Be sure to sample their signature IPA, ranked as the best in Oregon at the Northwest IPA Competition. Favourite whimsical offerings include Passionfruit Sour Ale, “Just the Tip” Spruced Wheat and Bourbon Barrel-Aged Aztec.

Happy Hiking at Wildwood Recreation Site: Located along the Mount Hood Scenic Byway near the town of Welches, Wildwood Recreation Site is a day-use area that is home to the Cascade Streamwatch Trail and Wildwood Wetlands Trail. Visitors have a chance to explore natural stream and wetland ecosystems along accessible interpretive trails and boardwalks and observe native fish in a unique underwater fish-viewing chamber. This 550 acre forested park includes outdoor kitchens, scenic picnic site and  ball fields.

Refreshed at Little Zig Zag Falls: This trail follows the Little Zigzag River upstream to the trail’s end at Little Zig Zag Falls. Visitors enjoy a cool and pleasant hike here on hot summer days, nothing too strenuous so a perfect spot to bring the family. The road visitors drive to reach the trailhead travel over parts of the original Barlow Road, which Samuel K. Barlow opened as a wagon route over the Cascades in 1846 to complete the Oregon Trail.

Zip Lining at Tree to Tree Adventure Park: Start your morning off with a wee adrenalin rush at Tree To Tree Adventure Park, an aerial ropes course and guided zip-line park. This “playground in the trees” features an aerial adventure ropes course with six courses of varying difficulty, each with 10 obstacles to master before zipping back to the ground. Be sure to face your fears via Woody’s Ziptastic Voyage, a zip line tour featuring six extreme zip lines (including one that is 1-280 feet long) a bridge and 40-foot rappel.

Vino Sips at Montinore Winery: Established in 1982, Montinore Estate is a family-owned vineyard and winery, and is among the top 25 producers of Oregon wine (in terms of number of cases), as well as the largest certified biodynamic/organic wine producer in the state. Among the varietals produced are Pinot Noir, Pinot Gris, Gewurztraminer, Riesling and Muller Thurgau. Be sure to sample a splash of the White Pinot Noir, an unusual vino with hints of quince paste, coconut and granny smith apple.

A Taste of Japan at SakeOne Brewery: No visit to the Tualatin Valley is complete without a visit to SakeOne, the leading American owned and operated brewer of craft sake in America. Bottled under four distinct brands (Momokawa, Moonstone and G), SakeOne leads the fast-growing category with distinct styles, flavour infusions and a penchant for educating its visitors. I sipped through the entire range and was most smitten with the Moonstone flavour infused collection. Be sure to sample from their Asian Pear, Plum, Raspberry and Coconut Lemongrass offerings. You’ll be inspired to shake up a few new creative cocktails.

Tranquility at Lan Su Chinese Garden: A year-round wonder, the Lan Su Chinese Garden is an authentically built Ming Dynasty style garden. Covered walkways, bridges, pavilions and a richly planted landscape frame a picturesque lake in this urban oasis built by artisans from Portland’s sister city of Suzhou. The Garden teahouse serves light snacks and traditional teas while public tai chi sessions take place on the terrace.

My visit to Portland was a press trip coordinated by Travel Portland. Transportation, accommodation, restaurant visits and activities featured in this destination guide were complimentary. 

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