Quirky Portland has gained a reputation as a hippie hang out, a refuge for an assortment of characters not too far removed from those free spirits and bohemians featured on IFC’s “Portlandia.” But Portland is more than just a caricature of itself. It’s a fantastic travel destination, a mid-sized city with great public transportation, a compact, vibrant downtown, and great day trip options to consider for a long weekend.
Here are our tips for whiling away a long weekend in Portland, Oregon:
Day 1: Go sightseeing
Portland’s scenic surroundings are a great way to unwind after a day of traveling. Parks, overlooks, and viewpoints abound here. In fact there are more than 10,000 acres of parks and natural areas, including one of the largest municipal parks in the country, Forest Park.
But for the occasional paved road through this 5,100 acre swath of temperate rainforest, you may have a hard time remembering you’re within Portland’s city limits. Four miles of well-maintained trails crisscross the park. Stop by the park’s other reminder of civilization, the Pittock Mansion, built in 1914. The grounds are free, have outstanding views, and make a nice place for a picnic—especially at sunset.
Among its many nicknames, Portland is known as “The Rose City.” Roses once lined the streets of downtown, and while that’s largely a thing of the past, visitors can still view a fantastic collection of hybrids at the International Rose Test Garden. Opened in 1917, the garden is 4.5 acres of rose bushes and walking paths. The blooms start around mid-May to late June and can flower until mid-October. A less crowded alternative is the nearby 5.5 acre Japanese Garden, which is actually made up of five separate gardens and boasts views of Mount Hood, Portland’s neighboring volcano.
Portland Aerial Tram
A cheap way to take in the skyline and surrounding mountains is to ride the aerial tram for just $4 round trip. The gondola-style tram is primarily used by commuters traveling between downtown’s South Waterfront and Oregon Health & Science University, but tourists should take advantage, too. On a clear day, you can see nearby volcanoes Mount Hood, Mount St. Helens, and Mount Adams. At night, the lights of downtown sparkle below.
Day 2: Shop Portland
Portland is a city of creative thinkers and artists who make purses out of bike tubes and stencil birds onto canvas bags and t-shirts. Storefronts and outdoor markets around town are full of reclaimed, upcycled, and vintage crafts and clothing. It’s like Etsy exploded onto the city.
And while other West Coast cities like Seattle and San Francisco have expensive shopping options, Portland has stayed fairly inexpensive, (stats show Portland is 19 percent cheaper than Seattle) and there’s no state sales tax in Oregon.
811 East Burnside Building
This building is home to various galleries and boutiques with reasonably priced, handmade and vintage crafts—the sort you can only find in Portland, like frames made from salvaged bike parts and brooches made from buttons. Favorite stores include Redux, featuring products from 300 artists, and Sword + Fern, with vintage finds and funky housewares.
Portland Saturday Market
Portland’s sprawling craft market (which is held on both Saturdays and Sundays, year round at the North Waterfront Park and Ankeny Plaza) features hundreds of vendors with vintage and handmade treasures. Add in street performers and food trucks, and it’s easy to spend a half a day wandering through the market.
Hawthorne Street is a lively street packed with shops and restaurants. The best are along Hawthorne from 11th to 55th streets, in the city’s southeast quadrant. Vintage clothes, crafts, and art abound here, as do some of the city’s best restaurants and drinking establishments. Check out the Bagdad Theater and Pub, where you can catch a movie while dining on pizza and craft beer. A favorite is The Dollar Scholar, where the weird trinkets are just a dollar and the owners will entertain you the moment you walk in the door. The popular boulevard offers plenty of people-watching, too.
Powell’s City of Books
Powell’s flagship store takes up an entire city block and has over one million new, used, and out of print titles. It’s easy to get lost here, but maybe that’s your intention by visiting. Powell’s on Hawthorne is smaller (though that’s not saying much) and tends to be less crowded.
Day 3: Get out of town
Portland is close to both the mountains and the ocean, surrounding by hiking opportunities and even several wineries, so there’s plenty to explore in the area without spending too much time in transit. It’s an hour and a half drive to Ecola State Park on the Pacific Ocean, and just over an hour to the Timberline Lodge and ski area on Mount Hood, making both areas manageable for a day trip or a weekend excursion.
Mount Hood National Forest
Mount Hood is the closest volcano to Portland, just twenty miles east and an hour and a half’s drive from downtown. Year-round skiing is available at the Timberline Ski Area on the mountain’s snowfields, and there are almost 100 miles of hiking trails in the immediate area. A worthwhile—though popular—pick is Mirror Lake, which offers classic views of the mountain and its reflection. Fewer people continue up Tom, Dick and Harry Mountain, which adds a couple of miles to your trip but offers expansive views.
Columbia River Gorge and Multnomah Falls
The Columbia River Gorge National Scenic Area protects the 80-mile swath of canyon comprising much of the border between Oregon and Washington. Outdoor activities here abound, including hiking, whitewater rafting, and windsurfing. There are also scattered wineries, museums, and galleries. One of the most popular attractions—and one of the closest to Portland—is Multnomah Falls, tumbling 620 feet into the river.
Ecola State Park and Cannon Beach
It’s an easy hour and a half drive from Portland to the Pacific Ocean, and one of the best places to experience it is Ecola State Park. The park offers picnic areas and hiking trails in sight of the iconic sea stacks and soaring cliffs that have made the coastline in the Pacific Northwest famous. The town of Cannon Beach, near the park, offers places to stay and shopping.
Eating and Drinking
One of the most famous eating options in Portland are the city’s food carts, which gather at designated parking lots to serve up everything from barbeque to Thai to Mexican. Sometimes the choices can be overwhelming and there’s not always a place to sit, but the food is always excellent and inexpensive. A good pick for a casual dinner is the Kennedy School, operated by McMenamins. The former elementary school now houses a bar, restaurant, hotel, soaking pool, gift shop, and movie theater. I suggest checking out the boiler room.
If you’re looking for something slightly more upscale, but still affordable, try Le Bistro Montage, where you’ll sit at communal tables and dine on southern-inspired soul food. For dessert, head to Voodoo Doughnuts, another Portland institution, where they serve bacon bars and cereal-covered treats. There’s almost always a long line (and hardly any seating) at the downtown location, but the NE Davis St. location is more civil.
Portland is home to some of the country’s best craft breweries, and you could easily spend an entire long weekend simply hopping from brew pub to brew pub. Expand your horizons with sour beer at the Cascade Brewing Barrel House, try barrel aged brews at Lompoc, and check out better-known Rogue Ales and Deschutes. Other great places to knock back a pint include Upright Brewing, Hopworks Bikebar, Bridgeport, Amnesia Brewing, Alameda Brewing, and Caldera Public House.
Read more about Portland’s Foodie Scene
- Megan Hill