Day 1: Explore Southwest and Northwest
Start your day with an organic breakfast at Wildwood, where everything's sourced in the Pacific Northwest.
Head up to the green hills of Washington Park and meander through the Japanese Garden, the International Rose Test Garden, the Hoyt Arboretum, the Oregon Zoo and more. You could spend the entire morning up here, taking in sweeping views of the city, the Cascade Range and learning about nature.
At lunchtime, swing over to upscale Nob Hill, which is also known as the Alphabet District; all the east-west streets here are in alphabetical order and named for a different person, place or thing in Portland history. Tuck into a hearty, artisanal sandwich at Besaw's, then take yourself boutique shopping along leafy NW 23rd Street. Catch your second wind with an Austrian pastry and coffee mit schlag at Papa Haydn.
If you feel like walking, hit the trails in Forest Park and luxuriate in a canopy of tall trees, rushing streams, mossy rocks and an aviary's worth of native birds. If you'd prefer a drive, wend your way over to the nearby Columbia Gorge and breathe in the forest through your car windows, making sure to stop at towering Multnomah Falls to feel its spray. If you're up for another attraction, visit the stately Pittock Mansion for a look back at Portland's beginnings and to gaze at the endless city view.
For dinner, tuck into dishes from all over Mexico and Portland's best margaritas at Por Que No?, or head to the Mississippi Marketplace to sample the wares of permanently-stationed food carts. Afterwards, try to catch a play at the Portland Center Stage, which makes its home in the former Portland Armory.
Day 2: Explore More of the Southeast and Northeast
Head to Mt Tabor Park for a morning hike, keeping an eye out for glimpses of Mt Hood, downtown Portland and wildlife.
Tuck into a Country Skillet breakfast at Dufour's in residential Irvington, then take a stroll to see some of the city's most elegant, historic homes. Visit Grant Park's Beverly Cleary Sculpture Garden, which features bronze statues of characters of children’s author (and Portland native) Beverly Cleary.
Go explore the corrugated steel charm of the Alberta Arts District, which is full of small galleries exhibiting the work of local artists, and stop into the colorful Tin Shed for a friendly lunch. Then take yourself over to the Buckman neighborhood for hipster boutique shopping and a crawl along the area's many micro-breweries.
For dinner, indulge in the farm-to-table delights of clarklewis, which sources almost all of its ingredients from local, sustainably-run farms. Nearby, catch an indie music act at the Doug Fir Lounge, or head to the 1920s vintage Alberta Rose Theatre to attend a raucous taping of Live Wire Radio!, a locally-produced variety show featuring comedy, musical acts and compelling interviews with writers.
Day 3: Explore Downtown
First thing in the morning, grab a local Stumptown Roasters coffee and go for a stroll beside the mighty Willamette River. At the Tom McColl Waterfront Park, you can check out "The Portland," a still-working steamboat often docked by the seawall, read occasional plaques that illustrate the city's history and watch fishing boats and rowing sculls sluice along the river.
Head to the north end of the park to explore the Saturday Market (Saturday, 10am-5pm and Sunday, 11am-4:30pm), a sprawling warren of tented stalls offering locally-made crafts, food and more. Nibble your way through the Market, or head to nearby Mother's Bistro for homemade biscuits in an airy, Victorian-era dining room hung with chandeliers.
Take an hour's meander through Asian and Native American artwork at the Portland Art Museum, then go lose yourself in the stacks at the enormous flagship Powell's City of Books. Take a few blocks' walk from there to the leafy North Park Blocks in the Pearl District, followed by a poke around the Museum of Contemporary Craft and the neighborhood's many art galleries and independent boutiques.
Indulge in some live jazz and afternoon tea at the historic Heathman Restaurant, or yet more coffee at Spella, which uses a hand-pumped, piston-driven espresso machine. If you're up for one more attraction, head through the ornate arches of Chinatown and visit the graceful water lilies at the Portland Chinese Garden.
Also in Chinatown, enjoy steamed Chinese pork buns and drinking-vinegar cocktails at Ping, or head to the nearby Via Tribulani for thin-crust Neopolitan-style pizza baked in a traditional tiled oven. Try to leave room for a quirky, jelly-oozing Voodoo Doughnut, then catch a movie and a glass of Oregon wine in a big leather armchair at the swanky Living Room Theaters.