Follow the Willamette River south, past Portland State University and Lewis & Clark College, and you’ll eventually reach the sylvan hills of Lake Oswego. In the early days — back when it was a humble assemblage of iron smelters, lumberyards and homesteaders — travelers could only reach Lake Oswego via the lazy river or bumpy dirt roads. Perhaps that’s why, though only 20 minutes from downtown Portland, the city still feels a world away.
Far removed from its modest origins, Lake Oswego now hosts beautiful homes nestled in misty pockets of the hills, and a charming downtown reminiscent of a ‘50s reverie. Whether you’re hitting the links, shopping designer consignment or sipping drinks on a shoreside patio, you’ll enjoy the tranquility Lake Oswego affords.
Start your day at NOLA Doughnuts, armed with a chicory coffee and a beignet piled so high with powdered sugar that it resembles Mount Hood. If the French Quarter isn’t French enough for you, there’s also the flagship La Provence boulangerie and patisserie, with pastry cases full of Instagram-ready delectables.
You know you’re at a great barbecue spot when the tables are stocked with toothpicks and wet wipes. Pine Shed Ribs serves up an Oregon riff on Santa Maria-style barbecue, smoking the dry-rubbed meat to perfection and pairing it with homemade barbecue sauce. For more excellent eats, travel back to a time of sock hops and drive-ins at Lake Oswego Ice Creamery, a classic diner that also offers a great selection of salads and vegetarian options. Slide into a bright blue booth and order a burger and shake — you won’t be disappointed.
Proper high tea awaits at Lady Di’s British Store and Tea Room, where patrons nibble on cucumber sandwiches and scones topped with jam and Devon cream as they sip tea poured from a cozied teapot. Expats can even stock up on their favorite English goods, like ploughman’s pickle, HP Sauce and all variety of Cadbury treats.
Kyra’s Bake Shop offers way more than just sweets — the entirely gluten-free kitchen serves up homemade soups, salads and breakfast plates that charm gluten-lovers and abstainers alike. And the cupcakes! Le Cordon Bleu-trained Kyra Bussanich’s expansive rotating menu doesn’t have a single dud on it, as evidenced by her three Cupcake Wars wins.
Built along the Lake Oswego shoreline, the historic Lake Theater and Cafe has been showing movies since 1940 and recently expanded to offer a full bar, café menu and live music. For a post-flick drink, sample a flight of brews at adjacent Stickmen Brewing Company, where an enticing outdoor patio hovers over the shimmering lake.
If you’re in town on Sunday, be sure to visit the picturesque Oswego Hills Vineyard and Winery for a complimentary wine tasting. Perched atop a grassy hill, the vineyard offers sweeping views of the surrounding area, including Luscher Farms, an urban farm-cum-park with walking paths and gardening plots. Walk the 4.4 mile (7 km) loop through the farm and over Cook’s Butte, keeping an eye out for blackberries when they’re in season.
If you prefer to stroll through downtown, the Arts Council of Lake Oswego organizes a walking tour of its Gallery Without Walls, a collection of over 60 sculptures scattered about town. Or wander around Millennium Park, the site of Lake Oswego’s cheery farmers’ market spring through fall, and outdoor movies and concerts in the summer.
One of the most city’s most popular attractions, the loamy Lake Oswego Public Golf Course features a cheery creek meandering through its 18 holes, as well as gorgeous views of Mount St. Helens and Mount Adams. To explore the tree-shrouded hills of Lake Oswego via the many miles of pathways the city has created, take advantage of Lakeside Bicycles’ bike rental program or allow the family-run business to fit you for your very own dream cycle.
The consignment shops in this prosperous city are more upscale than your average Buffalo Exchange, making it a cinch to score designer finds. Simply Posh and Consigning Women both have highly selective collections of designer bags, shoes, clothing and authenticated jewelry for discerning fashionistas — and the former has offerings for fashionable men as well.
Shops Francesca’s and Grapevine offer trendy clothing selections for women, while Patrick James, a small West Coast high-end menswear store, offers preppy styles à la J. Crew. Find them all in the Lake View Village downtown.