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Portland's East Side Story

Ride Portland's new streetcar to the city's edgier side for brews, bites, and eclectic boutiques.

  • clams and cod dish at Le Pigeon in Portland, image
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    A carrot slaw tops Le Pigeon’s clams and cod.
  • glasses of beer at Hair of the Dog Brewery, Portland, image
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    The Hair of the Dog brewery serves flights of craft beer.
  • kayak on the Willamette River, Portland, image
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    Alder Creek Kayak & Canoe’s Paul Kuthe leads excursions along the Willamette’s urban shores.
  • man makes coffee at Coava Coffee Roasters, image
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    Jeremy Richards multitasks at Coava Coffee Roasters.
  • Portland streetcar, image
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    The city’s new streetcar crosses the Broadway Bridge.
  • two people kiss at Portland streetcar stop, image
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    Two people share a smooch at a streetcar stop in Portland.

Like most visitors to Portland, I headed downtown on arrival. The Ace Hotel was just as retro-groovy as they say, and then there was Voodoo Doughnut, Powell's Books, Stumptown Coffee Roasters, and Voodoo Doughnut again later that night. But with apologies to the city's lovely hub, my interest during this trip lay in leaving it. I'd come to make my way to the east side of the Willamette River.

On past visits, seeing the other side of town had meant climbing into a car—a hassle, if not a contravention of the city's green, alternative-everything ethos. But this past fall brought the Portland Streetcar Loop Project, a 3.35-mile route that takes off from the existing line, crosses the Broadway Bridge, and then runs south, parallel to the river. By 2015 you'll be able to circle back to downtown across the future TriMet Bridge—hence, "the Loop."

Once upon a time, Portland was swarming with streetcars. Horses dragged the first one along Southwest First Avenue in 1872, and soon the city was crisscrossed with tracks. But buses and cars ruled by the 1950s, and across the country trolley tracks were melted for scrap.

It had been 64 years since a trolley had crossed the Broadway Bridge, Mayor Sam Adams informed Portlanders at the Loop's ribbon-cutting ceremony. (Do you really need to ask whether a marching band showed up at the festivities?)

Now, checking out Portland's edgier half is as simple as feeding a dollar into a machine (or $5 for a day pass). The best way to take advantage? Simply cruise up and down, popping off here and there to explore. On a brisk morning, that's exactly what I did, starting at one of the stops on 10th Street downtown. In no time, a silent, futuristic caterpillar eased up to the curb. I climbed aboard, and within minutes I was on the other side of the city. Pressing my nose to the brand-new glass, I let the neighborhoods scroll past.

The vibe changes instantly when you cross to the east side of the Willamette River: Shirts untuck. Traffic abates. Stylish condos vanish, replaced by cute mom-and-pop shops and an endless supply of warehouses. Industrial zones in hip cities tend to suffer from too many overpriced lofts and too little actual industry. But here the forklifts are real. Downtown Portland isn't exactly Tokyo, but the east side is nonetheless calmer and leafier, not to mention funkier; the plug-earring-per-capita numbers rise markedly.

The Lloyd and Central Eastside districts, which together are the Brooklyn to Portland's Manhattan, host the bulk of the streetcar extension and are fat targets for top-shelf connoisseurship; everyone's got a favorite unsung restaurant, brewery, café, or thrift store. Normally a map-free sort, I was glad for the recommendations I'd jotted down. This part of town is still fairly industrial, and if you don't know what you're looking for, you may not find it. Of course that's also part of the appeal.

It helps if your hunt is, at least in part, for a drink. Portland famously has 51 breweries—more than any other city in the world—and many are located right here. There's the Cascade Brewing Barrel House, beloved for its terrific and thoroughly odd sour beers. The Hair of the Dog Brewing Company and Tasting Room, approaching its 20th year, is beer aficionado territory—yet still welcoming to novices. Sitting in the breezy, garage-type space, surrounded by a flannel-and-fleece crowd, I was glad to find a culture utterly without airs. How pretentious can you be while sipping a barley wine called Doggie Claws?

In the hopes of appeasing the artisanal alcohol gods, I rolled on over to New Deal Distillery, part of what's called Distillery Row. With the same pioneering instincts that brought the brewing scene to Portland, a handful of enthusiasts is reinventing the way spirits are made: Instead of churning out big, soulless productions, they're lovingly crafting hooch in tiny batches. I sat for an incandescently spicy Hot Monkey vodka and promised to return one day for a full tour of all five spots.

The Eastside district is not all about alcohol. Three stops north of New Deal Distillery lies a big 1920s building once brimming with Wheaties. The refurbished Olympic Mills Commerce Center, no longer in the cereal business, has become home to a number of inventive thimble-size stores, restaurants, and offices, from the Zimbabwe Artists Project gallery to Olympic Provision—Oregon's first USDA-approved, much-drooled-over salumeria—to the legendary Kill Rock Stars record label that signed Elliott Smith, Sleater-Kinney, and the Decemberists, to name a few. (Alas, you can neither shop for records nor swoon at the musicians.) I explored the center's halls, feeling I'd stumbled into a miniature Portland: an olden days relic remade as an epicenter of crafts, art, and gastronomy.

Anchoring the southern end of the streetcar's route is the Oregon Museum of Science and Industry with its planetarium and IMAX theater—one of Portland's biggest draws. Nearby, at Alder Creek Kayak & Canoe, you can launch out onto the river to see the urban landscape from the water.

But it was time for another ride, this time for refueling at Coava Coffee Roasters. If you currently don't drink enough finely sourced, small-batch java in spacious, spare concrete industrial spaces shared with sustainable-bamboo timber companies, you're in luck. (Yes, you can sip your espresso at a drill press.) The tidy young gentleman behind the counter welcomed my middlebrow coffee tastes with open arms and a cup of something allegedly bearing blueberry notes. I nodded intelligently.

It was at Coava that I got to talking with a local who claimed that Portland is the kind of city where you can ask a stranger for a dinner recommendation and score a seat there that same night, no matter how fancy it is. Three separate locals had insisted I eat at Le Pigeon, a wildly inventive French restaurant, so I hopped back on the streetcar to Burnside Street. After strolling a few blocks along a strip of Portlandia-ready boutiques—vintage clothing, funky gifts, a highly curated smorgasbord of art and books—I bellied up to the restaurant's bar. Within minutes I was deep into a menu of rabbit and eel terrine and foie gras miso vinaigrette—dishes that had sadly been missing from my life until now. Same, apparently, for the fellow to my left. So delighted was he that he offered a bite to the utter stranger he'd been chatting with.

"People here just decided life's easier if we're all very nice to each other," my old friend José Klein told me later that night.

José, a young lawyer who, in true Portland fashion, satisfies his creative side by making artwork about legal history, moved to the Eastside from San Francisco several years ago. I had invited him to poke around near the new tracks with me that night. We strolled happily, at one point wandering into an old building on Southeast Main Street where people can play—or in our case watch, and buy beer while watching—indoor soccer. It wasn't a big thing; it was a tiny, quirky thing, and sort of lovable for it.

Ostensibly I had come to the City of Roses to ride the new rails. But any visit to Portland invariably turns into a scouting mission: a consideration of that mellow, crafty life of sprawling afternoons magically structured around microbrews and bikes. Whether you're from the other side of the country or simply elsewhere in Oregon, the sheer livability of the place leaps out.

Will the new streetcar make things even better? That's the vision—more housing development, more tourism, more shops, restaurants, and galleries to go with all the breweries—though there are skeptics. (Those buses that replaced the streetcars half a century ago? Turns out they still have their fans.)

José and I parted company, but I wasn't quite ready to turn in. Drawn by the thump-thump-thump, I ventured into the Doug Fir Lounge, a hopping and vaguely swanky spot for live music. I flashed my ID and spent the next hour dancing.

Time runs out quickly in Portland. I could've stayed much longer, ridden the rails one more time—but the next morning I had a cousin of a streetcar to catch: the light-rail to the airport. I made my flight with minutes to spare, half wishing I hadn't.

Photography by Don Frank

This article was first published in March 2013. Some facts may have aged gracelessly. Please call ahead to verify information.