Day 1

Spend your first day in Portland seeing the downtown area. With its compact blocks and interesting mix of buildings, architectural styles, and parks, downtown Portland is easy to walk (or bike) and a pleasure to explore.

Start right in the heart of downtown at Pioneer Courthouse Square, referred to as “Portland’s living room.” Here you’ll get a feel for the city’s face and fashions as commuters get off the buses, streetcars and MAX light-rail lines that flank this transportation hub. A big Starbucks on the southwest corner of the square has outdoor tables where you can sit in nice weather watching the passing parade and looking out over the waterfall fountain and zany weather machine. Pioneer Square is downtown shopping central, with a flagship Nordstrom right across from the square and most of downtown’s major stores within a four-block radius. Grab lunch in midtown.

Head up to the South Park Blocks, just a couple of minutes’ walk, and have a look around the Portland Art Museum, especially its Native American collection. This should take about 2 hours. From the museum, walk south to a few blocks to have a look at the waterfall-like Ira Keller Fountain, a splashing evocation of Oregon’s cliffs and rivers. From there, head down Salmon Street four blocks to Tom McCall Waterfront Park, where you can stroll along the esplanade with Portland’s skyline on one side and the river with its historic bridges on the other. Jake’s Famous Crawfish, Portland’s oldest restaurant, is an atmospheric choice for happy hour or dinner. The easiest way to get there from waterfront park is to take Stark St. west through downtown for 12 blocks. It won’t take more than 15 minutes.

Day 2

Head first to the Oregon Historical Society Museum on the South Park Blocks, across from the Portland Art Museum, for a compelling look at Oregon’s and Portland’s pioneer and more recent history, as well as its Native American roots. You’ll likely want to linger for about 2 hours at the museum, as there are many short videos, audio posts and artifacts to examine.

Then its lunch at one of Portland’s famous food carts. They are found at various locales around downtown, though we recommend both the “pods” of carts at SW 9th and SW10th avenues, as they have some stellar options. To see the offerings at other carts visit

For over a 100 years Portland has been called the City of Roses. So now it’s time to smell these blossoms at the 100-year-old International Rose Test Garden in Washington Park in the southwest hills. Take MAX (the light-rail), drive, bike or walk (it’s about a half-hour steady walk from downtown) to marvel at this dazzling display of tens of thousands of roses on a hillside overlooking downtown and Mount Hood.

After you’ve sniffed and snapped (with a camera) your fill of roses, head up to the Portland Japanese Garden, on the hillside directly above the rose gardens. This superlative garden will introduce you to an ancient and entirely different gardening style. There’s never been a better time to visit. In 2017 the Portland Japanese Garden opened a $30.5-million expansion by famed Japanese architect Kengo Kuma that transformed the central plaza and added striking new buildings that house the gift shop, performance spaces and a glass-walled teahouse.

There really aren’t any places to eat right in the park, so make your way back downtown to enjoy happy hour at any one of Portland’s restaurants, or a dinner at someplace special, like Tasty n Alder. After dinner, head over to mega-store, and literary powerhouse, Powell’s City of Books, which is open late every night of the week and often hosts terrific book signings and other events.

Day 3

It’s time to explore a Portland neighborhood and the largest urban forest in North America, with a stop at one of Portland’s largest and most scenically-sited historic homes. Start the day at Caffe Umbria, the nicest coffee bar in the Pearl District. Afterward, explore the Pearl, which has been transformed over the past 20 years from an industrial area of low-rise warehouses to a dynamic mix of art galleries, new residences and parks, with an ever-expanding restaurant and shopping scene. I’d recommend stopping in at the Bullseye Gallery, just a block away from Caffe Umbria, because they always show impressive works that break the boundaries of glass (but don’t break the glass itself). The Pearl is a good spot to have lunch, too.

After strolling through the urban Pearl, a leafy change of pace is in order. Catch the Portland Streetcar going south to Burnside St. and then the 20 bus heading west up Burnside. Ask the driver to drop you off at the stop for Pittock Mansion at Burnside and NW Barnes Rd. If you’re driving, the directions are the same, only you’ll turn into the curving drive that leads up to the mansion’s parking lot. If you’re on foot, you’ll follow an easy uphill trail to reach the mansion’s entrance, or take the free shuttle bus that runs from June through Labor Day. The enormous French Renaissance Revival chateau, completed in 1914 on a 1,000-foot-high crest in Forest Park, is the largest and most opulent historic house in Portland. Take one of the 40-minute tours offered throughout the day to learn more about this historic landmark and its role in Portland’s history. After touring the house, filled with rare woods and marbles, walk down to the viewpoint at the end of the lawn to enjoy one of the best all-around views of Portland, including three mountain peaks.

If you’re in the mood for a hike, the Wildwood Trail at the end of the parking lot will take you downhill through Forest Park to Thurman Street, but that’s at least an hour’s walk. Alternatively, make your way back to Burnside on foot or on the shuttle bus for a return trip downtown on the 20 bus. For dinner, head over to SE Division, one of the city’s newer restaurant rows, to dine on authentic Thai street food at Pok Pok or fabulous Italian cuisine at Ava Gene’s.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.