What’s a walk in the park, a picnic on the grass or an outdoor patio to sip wine without a river to gaze at? How about a soothing river paddle, just minutes from the city? There’s a scientific reason why water is so calming — a source of creativity and inspiration and relaxation. You don’t even have to leave the city to access the river in four vibrant urban communities that are part of the region known as Mt. Hood Territory. In fact, when you’re downtown in Oregon City, Milwaukie, West Linn and Lake Oswego, you’re just blocks away from easy access to the Willamette River, the lifeblood of the region. Here’s what to do on a river-inspired getaway in the city.
Downtown Milwaukie
Milwaukie’s Main Street, southeast of Portland on the east bank of the Willamette River, is easily accessible from Portland by light rail on the MAX Orange Line. Steps from the MAX line, a “Welcome to Milwaukie” mural honors Ah Bing, creator of the Bing cherry, along with Dorothy and Hurtis Hadley, who ran the state’s first Black-owned bakery.
Come hungry — Milwaukie Station Food Cart Pod offers a range of global street food with plenty of covered picnic tables. Or indulge in an afternoon of martinis and shareable small plates across the street at Decibel Sound & Drink, a top cocktail bar. For French-Asian fusion, visit Ovation Bistro, or head north for the Beer Store Milwaukie, offering dozens of local craft beverages on tap plus a large selection of Impossiburgers and flatbread pizzas to nosh on. Pick up a locally made memory from Made in Milwaukie. One block west of Main Street, Milwaukie Bay Park anchors downtown, complete with a boat launch and an amphitheater-style lawn for picnics and performances. Take a walk or bike ride along the Trolley Trail, a 6-mile paved, car-free path that connects Milwaukie to neighboring Gladstone.
Downtown Lake Oswego
Across the river from Milwaukie on the west bank of the Willamette, downtown Lake Oswego sits at the northern tip of Willamette Falls & Landings Heritage Area. Learn more about the city’s early roots while exploring the Oswego Iron Heritage Trail, which guides visitors to seven sites including the Oswego Iron Furnace and the Iron Workers’ Cottage, now a museum.
Today downtown Lake Oswego is known for upscale boutique shopping and dining. In Lake View Village, across from Oswego Lake, find independent shops like Grapevine Fashion and Mapel Boutique and Wishbone Home & Design. For lakefront dining, head to Five Spice Seafood + Wine Bar for a Dungeness crab and bay shrimp melt or Pizzeria sul Lago for some of the best Neapolitan-style pizzas and pastas in the region. Take a half-mile walk to George Rogers Park on the Willamette River, one of the city’s many beautiful parks. Along the way, stop and admire the outdoor nature-inspired sculptures that are part of the city’s Gallery Without Walls. At the park, you can rent seasonal kayaks and stand-up paddleboards from Alder Creek Kayak Canoe, or book a guided paddle tour to nearby Hog Island.
Historic Willamette Main Street
Just south of Lake Oswego, also on the west bank of the Willamette, historic Willamette Main Street sparkles with small-town charm. Wine star Allium bistro creates locally inspired fare like foraged-mushroom pizza to pair with more than 50 wines by the glass. Gather round the fire pits at the heated, covered outdoor beer garden at Ale & Cider House at Willamette, or sip a Cherry Blossom cider with food-cart fare on weekends at the adjoining Queen Orchard Cidery. Four area wineries — twill cellars, Tumwater Vineyard, Campbell Lane Winery and Pete’s Mountain Vineyard & Winery — are within minutes of downtown, making for an easy afternoon sipping rosé on a patio with vineyard views.
Also downtown in West Linn, visit the historic Leisman/Elligsen House and pick up the Historic Willamette Walking Tour booklet, which guides you through the Willamette Historic District. A quick walk south takes you to Willamette Park, where the Tualatin River meets the Willamette River. Open seasonally, eNRG Kayaking hosts an annex here, renting flatwater boats and stand-up paddleboards to explore on your own.
Downtown Oregon City
Oregon City, on the east bank of the Willamette and across the river from West Linn, is best known as the official end of the Oregon Trail. Pioneers settled here in 1843 after their 2,000-mile journey, using Willamette Falls to supply power to mill lumber and as a plentiful source of salmon and sturgeon. Indigenous Tribes used to trade and fish at these falls for salmon and lamprey, and some still do. Oregon City soon became a bustling community of orchards and dairy farms, boatyards, flour mills, and other businesses. Downtown Oregon City retains this pioneering spirit. You can see it in specialty shops like White Rabbit Gifts, for curated books and local goods; Refinery, consignment dedicated to conscious consumerism; and Margaret & Maxwell, specializing in midcentury-modern and vintage pieces. Women-owned Root + Stem Plants offers gorgeous plants and easy plant-care help to aspiring greenthumbs.
A half-mile walk from downtown takes you to the riverfront and the headquarters of eNRG Kayaking, with rental kayaks, paddleboards, canoes and fishing kayaks. Or book a full-moon paddle, an evening of live music on the water or a morning PiYo and paddle. You can learn more about the area’s Indigenous and pioneer history on a guided tour of Willamette Falls — the second-largest waterfall by volume in the United States. Thanks to Willamette Falls Electric Boat Company, you can even captain your own vessel. Make it a picnic cruise with takeout from the new Corner 14 taphouse and food-cart pod, or a meat-and-cheese plate from Oregon City Brewing next door.
