It wasn’t too long ago that Portland, with its hip, one-of-a-kind stores and lively food scene, was the best-kept secret in the United States. Today, Stumptown—the city’s oldest nickname—is seducing visitors with its urban sophistication, natural splendour and small-town charm.

Culture Connoisseur

Photo by Jordan Hughes

Where to stay: Woodlark’s 150 sleek rooms are housed in two nationally registered historic buildings. There are plenty of visual touches for guests to discover, from the velvet, scallop-edged headboards and garden-themed wallpaper inspired by nearby Forest Park, to rugs by local designer Christiane Millinger.

What to do: The city’s creative scene is booming —and shoppable. Many of the unique products stocked at Tanner Goods, for instance, are made in the Portland area. Check out the selection of roomy canvas bags and leather wallets, and admire the Mazama brand’s sculptural, hand-blown wine glasses.

Where to eat: At newly opened, two-level Palomar (shown), expect to find palm tree illustrations, mid-century stools and bright tiles as part of its summer-in-Havana decor. Beef empanadas, jackfruit stew and the city’s most addictive frozen daiquiris seal the deal. Make sure to go there early as it doesn’t accept reservations.

Food Lover

Photo by Carly Diaz

Where to stay: The modern rooms at The Hoxton, Portland—located in Chinatown—are bolstered by three dining-and-drinking outlets that feature menus from executive chef Johnny Leach. There’s a basement-level cocktail space, a lobby restaurant, and Tope, a rooftop destination for tacos, carnitas and more.

What to do: Portland is full of cutting-edge artisans, such as Woodblock Chocolate, known as the city’s first bean-to-bar chocolate-makers. Sample seasonal offerings, including Meadow Kombucha, a chamomile blend with rose petals, at Smith Teamaker, which recently introduced tours on Friday afternoons.

Where to eat: One of the premiere Russian kitchens in the United States, Kachka is a welcoming destination specializing in comfort food from Eastern Europe (shown). The pelmeni, or Russian dumplings, filled with beef, pork, veal and onion, and the seven-layer herring, beet and egg salad will transport you back to the USSR.

Night Owl

Where to stay: Boutique hotel The Jupiter (shown), a renovated motor lodge from the 1960s, is outfitted with a quirky interior full of personality—some rooms come with full-wall illustrations of Spider-Man. The neighbouring Doug Fir Lounge is a hopping music destination that stages a live show nearly every night.

Photo by Jacob Williamson

What to do: Dance into the early morning hours at Holocene, a two-level nightclub which hosts a variety of events. From bombastic queer-pride parties and electronic DJ sets, to concerts from up-and-coming global indie bands, there’s something for everyone at this Portland institution located on Morrison Street

Where to eat: The menu at Abigail Hall’s is filled with whimsy: secret sauce-slathered Abby’s burger inspired by In-N-Out; everything-bagel-spiced crackers served with a smoked salmon dip; and The Dog Will Hunt, a cocktail that mixes Fernet Branca infused with charred pineapple and a whisky blended with Mexican Coca-Cola.

Nature Enthusiast

Where to stay: Despite its downtown location, Dossier hotel will add an outdoorsy, wellness twist to your stay. It has partnerships with Wy’East, which organizes complimentary weekly runs for guests, as well as health club Knot Springs, offering discounted access to its stress-busting spa with steam rooms and thermal pools.

What to do: Feel connected to the rugged Pacific Northwest landscape that surrounds Portland with Evergreen Escapes’ Whitewater Rafting and Wine Tour (shown). This fun outing takes guests down the rapids of the White Salmon River—a tributary of the Columbia River— followed by a visit and tasting at two nearby boutique vineyards.

Photo by White Salmon

Where to eat: Wine bar OK Omens’ innovative vegetable dishes (think roasted carrots drizzled with a black garlic hoisin sauce) balance a richer plate of egg yolk-loaded crab pasta. Its natural wine selection boasts the unexpected, such as La Perdida winery’s Alicante Bouschet, which is full of depth and spice.

[This article appears in the August 2019 issue of WestJet Magazine.]