If You Have 1 Day
Spend the morning exploring downtown. Visit the Portland Art Museum and—perhaps briefly—the Oregon History Museum, saunter past the historic First Congregational Church and through Pioneer Courthouse Square, and take a stroll along the Park Blocks and Waterfront Park. Eat lunch and do a little shopping in the West End in the early afternoon, and then continue west to admire the beautiful historic homes in Nob Hill. From here, drive up into the West Hills to Pittock Mansion, and finish off the afternoon at the Japanese Garden and—in summer—the International Rose Test Garden in Washington Park. If you still have energy, head across the river for dinner along Hawthorne Boulevard or Division Street; then drive up to Mt. Tabor Park for Portland's best view of the sunset.
If You Have 3 Days
On your first day, follow the itinerary above, but stay on the west side for dinner (the Pearl District has some terrific options), and take your evening stroll in Waterfront Park. On your second morning, visit the Lan Su Chinese Garden in Old Town, and then head across the river to check out some of the northern East Side’s hip and diverting neighborhoods, such as North Mississippi and Northeast Alberta Street—both are rife with excellent lunch options as well as interesting shops and galleries. Then head south to the Central East Side to explore OMSI and walk along the Vera Katz Eastbank Esplanade before venturing either to Laurelhurst Park or Mt. Tabor Park for some greenery and fresh air. In the early evening, check out some of lively bars, brewpubs, and restaurants in the Burnside and 28th, Hawthorne, and Division Street neighborhoods—many hangouts in these parts have wonderfully affordable happy hours, with great deals on booze and food. Both Division Street and the Burnside and 28th area are home to some of the city’s hottest eateries. On Day 3, take a morning hike in Hoyt Arboretum or Forest Park; then spend your afternoon exploring shops and galleries in the Pearl District, or back on the East Side, where you might revisit any of the neighborhoods you didn’t get a chance to spend sufficient time in the day before.