Itineraries for Your Trip to Portland
2 Days in Portland, Oregon for First Timers
Before I first visited Portland, Oregon, I knew it for its alternative streak. “Keep Portland Weird” is the city’s unofficial motto, after all, and Portlandia did an apt job of gently skewering its eclectic characters and artsy energy. Those factors first drew me to this resolutely quirky West Coast city, but once I arrived, I found so much more that sets Portland apart.
The city’s food cart pods, for example, offer some of the best dining around, and local favorite Powell’s City of Books claims to be the world’s largest independent bookstore. Portland is also within easy reach of some of the Pacific Northwest’s most dramatic waterfalls, forests, and hiking trails, including the Columbia River Gorge. Whether your tastes run more cultural or crunchy-granola, there are lots of ways to make the most of two days in Portland.
If you only have time for one thing, eat your way through part of Portland’s thriving food cart scene, one of the city’s claims to fame.
Portland is known for its mild, Pacific Northwest climate, with warm summers and rainy winters; pack layers (and hiking boots).
Need to find your feet in Portland? One of the best ways to discover a new city is to explore on a walking tour. Pick an itinerary that hits the city’s top attractions, from Pioneer Square and the International Rose Test Garden in Washington Park to Powell’s and the hip Pearl District. As you go, look out for Mt. Hood’s iconic peak in the distance.
One of Portland’s greatest claims to fame is its unique food scene—and that’s good news for your lunchtime plans. Once you’ve worked up an appetite with your morning sightseeing, dedicate your afternoon to a tour of the city’s food cart pods (large gatherings of food trucks). Exploring with a guide makes sampling the best bites easy.
Portland was founded in the mid-19th century, and over the years it has experienced a number of spooky events, unexplained happenings, and gruesome crimes. To learn about another side of the city, head out on an evening ghost tour of the Old Town area. You won’t just see some of the city’s most historic landmarks—you’ll also put your bravery to the test as you watch for spirits and specters.
Portland is perfectly positioned near beaches and mountains, rivers, and waterfalls, and no trip is complete without an excursion into the nature nearby. Take a morning tour of the Columbia River Gorge, and you can explore one of the Pacific Northwest’s top scenic highlights—and see storied sights like Multnomah Falls (Oregon’s highest waterfall) and the Portland Women’s Forum State Scenic Viewpoint—without taking up a whole day.
The best way to refresh yourself after a nature getaway? A taste (or several) of Portland’s craft brewery scene. This Pacific Northwest city has long drawn beer lovers with its wide range of bars and brewpubs; in fact, it has the most breweries per capita of any major US city. Tour breweries by bike to combine Portlanders’ favorite mode of transport with sips of some of its finest suds.
After all that activity and exploration, it’s time to take it easy in the evening—and enjoy a fittingly celebratory way to cap off your visit. A dinner cruise along the Willamette River, which wends its way through the heart of the city, is the ideal way to combine a hearty meal with some especially magical sightseeing. You’ll have a front-row seat as the sun goes down over the city.
