East Burnside Street, a major thoroughfare that runs through the Kerns neighborhood, is chock-full of eats, drinks, shops and inspiration that fueled Portland-native Matt Groening in creating “The Simpsons.” (The oft-evil and always wealthy Mr. Burns was named after the street and the hood’s Montgomery Park.)

From the Burnside Skatepark to multiple restaurants from award-winning chef-restauranteur Gabriel Rucker, East Burnside is also a look at “Old Portland,” with the Doug Fir Lounge concert venue representing up-and-coming musicians for decades and the quirky and quintessentially Portland Jupiter Hotel hosting guests from all over.


First things first, if you are a visitor to Portland and taking this drinking-and eating-tour, you need to set up a bed to crash in. The new Jupiter NEXT is a classed-up, trendier little sister to the original Jupiter Hotel, found across the street.

For example, instead of charming condoms in the bedside dresser and rock bands performing below your floor boards like the OG, you’ll find sleekly designed (yet classically Northwestern) rooms outfitted with 60-inch flat-screen TVs, mini fridges, WiFi and city views. Kick off your food and drink tour of the hood at Hey Love Restaurant + Bar, the hotel’s ground floor and tropics-inspired eatery. Exotic plants and local art coat the walls, James Brown is known to blare from the speakers and comfort food mixes with tiki-esque cocktails.


Hit the street for more to drink, starting at the no-frills taproom for Natian Brewery. Beers are another story: Try the Lifted Light Lager – available in a version with and without oak chips – a clean, yet malty sip kissed with hops, or the roasty, creamy Lumberjane milk stout. Found just off Burnside on Ankeny, Coalition Brewing might be best known for its CBD-infused IPA (Two Flower) but the compact taproom also sports a new patio and a variety of other creative suds like the Roselandia, a sweet-tart kettle-soured golden ale. Daily CBD voted it the best CBD beer – for two years running!

Another single-block deviation off of Burnside to Couch Street, the pub and production facility for Cider Riot! pours English-inspired, cider-apple-built sips like the 1763 alongside modern takes like the Everybody Pogo hopped cider. Wild Roots Spirits recently opened an off-Burnside tasting room to showcase its plethora of infused vodkas, like the very Oregon Marionberry vodka. The Distillery Row tasting room also samples its spirits in cocktail form.

For wine, hit fan-favorite wine bar Noble Rot for flights and a rooftop garden, or visit the lively Bar Vivant, where sherry and canned Spanish tapas (think sardines or shrimp in olive oil, plus salt cod fritters) share the spotlight. Get straight with coffee from Heart Coffee Roasters, where the contemporary cafe showcases the house roasts, alternative milks made in-house and a gorgeously woodworked communal table.


The most important meal of the day should be eaten at Screen Door, where Southern cuisine meets Oregon ingredients, like the buttermilk-battered fried chicken with sweet potato waffle and the bananas fosters French toast featuring Pearl Bakery brioche.

Tusk takes a likeminded approach of marrying a cuisine with Northwest eats, here taking Middle Eastern flavors to the plate with seasonal produce. Try whatever is freshest from the vegetable menu (like string beans with mint and lebneh) and anything fresh-caught or locally raised from the protein list (like the ground lamb and pork skewer or the Chinook salmon with corn and shiso).

Le Pigeon is the grande dame of Burnside eateries – not quite the oldest but one of the most respected and celebrated restaurants in the Rose City. “Fine dining in a relaxed atmosphere,” Pigeon brings together French fare with innovative cookery, like in the plum-glazed namesake bird with roasted carrots and the seared foie gras served with camembert and a squash waffle. Fork out for the chef tasting menus – available in five-and seven-course options, plus wine pairing add-ons – to fully experience what the kitchen (and the wine list) offers.

Scale it back just a bit at sister restaurant Canard located next door, where bird is still the word for eats like the fried chicken wings with truffle ranch and truffle honey, but the Instagram-popular steam burger brings folks in with good reason.