Few things characterize Portland, Oregon better than the slogan “Keep Portland Weird,” which captures the city’s quirky and hyperlocal side. If you are in town for a couple of days, check out what to do in Portland with this 2-day itinerary and discover the slightly weirder side of Portland.

What To Do In Portland In 2 Days

Day 1: Walk On The West Side

The area west of the Willamette River is densely built up and lends itself better to walking, as does Forest Park.

Visit The Waterfront

If Pioneer Courthouse Square is Portland’s living room, the Tom McCall Waterfront Park, colloquially known as the Waterfront, is its backyard. Here’s where festivals take place come spring, here’s where downtown workers stroll or eat lunch on their breaks, here’s where cyclists do the commuting. And here’s where you can sometimes spot a lone seal poking its head out of the water as it floats in the Willamette River.

Powell’s Books

When in Portland, the world’s biggest independent bookstore is an essential stop. Spanning a full downtown city block and four floors, Powell’s Books has its own map to guide visitors through miles of shelves in nine color-coded rooms. Resist the urge to follow the map and get lost instead.

Cameron’s Books and Magazines

Powell’s may be the biggest, but the city’s oldest bookstore, established in 1938, is even weirder. Cameron’s Books and Magazines, behind its new Human Wildlife-proof gate, is the only place where you’ll find a magazine from your birthday month and year; and if not, vintage Life or Playboy or pulp fiction mags are here to console you.

What To Do In Portland Oregon 2 day itinerary

Pittock Mansion

Keep walking to deep NW Portland for a hike to Pittock Mansion, which embodies Portland’s pioneer history at its grandest. Dubbed “Portland hiking at its best” by the local rag once edited by Henry Pittock himself, the actual 5-mile round trip begins at Lower Macleay Park, under the NW Thurman Street bridge. The trail winds along Balch Creek, past an abandoned building nicknamed Witches Castle, and up through the magical Forest Park.

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Tiny Horses

On the way through Alphabet District/Nob Hill neighborhoods, spot a few remaining Tiny Horses tied to historic rings on curbs. These are toy horses a local artist scattered around the city in 2005. In the ensuing years, hundreds of them neighed quietly at your feet, but today only a few remain.

Day 2: Bike On The East Side

Biking is a great way to discover Portland’s weird delights; East Side is more residential and leafier plus it’s criss-crossed with hundreds of miles of bikeways, so borrow a bike from your local friends, rent one at Everybody’s Bike Rentals, or check an orange one out with the Biketown bicycle sharing service, and explore the cool things to do in Portland by bike.

Yard Art

As you bike around South and Northeast Portland, spot folk art in Portlanders’ yards. Lawns or landscaping? Boring! The Portland spirit asks for throwing in some home-made sculptures, benches, fencing, or shelters to show off your creativity and delight the neighbors and passersby alike.

USS Blueback

things to do in Portland Oregon in 2 days

The U.S. Navy’s last non-nuclear attack submarine, USS Blueback, is permanently stationed in the Willamette River, just south of the excellent Esplanade and Hawthorne Bridge. Featured in the action movie The Hunt for Red October, there are daily and technical tours, the latter led by Navy veterans, and you can also sleep on the sub overnight.

Christmas Reading: The Ice Monster

St. Johns Bridge

The only suspension bridge across the Willamette River; the tallest bridge in Portland; built to look like a Gothic cathedral. St. Johns Bridge is the main attraction in the eponymous neighborhood, overlooking the aptly-named Cathedral Park, site of an annual jazz festival. Pair with a visit to Occidental Brewing.

Murals in the Central Eastside Industrial District

What To Do In Portland In 2 Days

The up-and-coming Central Eastside Industrial District is rich in fun places to go, including bars and restaurants. Add to the list a self-guided street-art tour which will take you by some 35 of the 100+ SE Portland murals, many of which exemplify the city’s spirit. Best go on Sunday when fewer delivery trucks and cars block views.

Hopworks Urban Brewery

If when thinking what to do in Portland you did think about places to have drink, remember that Portland boasts the most breweries of any American city, 70 at the last count. The greenest brewery in town, Hopworks Urban Brewery, or the HUB, always features plenty of beer options, both classic and experimental, and more than decent pub fare. If you’re lucky, you can enjoy your evening in an old safe room or by the fireplace.

Crystal Springs Rhododendron Garden

What To Do In Portland Oregon 2 day itinerary

The city’s hidden gem is a sprawling network of trails through rhododendron groves and ponds, offering a serene getaway from the city’s bustle and one of the most romantic things to do in Portland. Pair with a stroll around nearby Eastmoreland mansions or Reed Lake.

Laurelhurst Park

things to do in Portland Oregon - 2 day itinerary

The city’s most beautiful park is home to nearly 1,000 trees of 115 species, a pond, miles of trails, lawns, a majestic brick staircase, picnic tables, and an off-leash dog area. You can run, you can hide, you can picnic, you can lounge, you play the guitar, you can do tai chi or yoga, you can throw a Frisbee, you can dance at the silent disco, you can take a wedding or quinceañera photographs, you can volunteer to clean up or landscape… or you can just be, because Portland doesn’t get any better than this.

Photos: All photos by Peter Korchnak, except for the feature image (CCO Creative Commons)

The Author: Peter Korchnak is a co-founder of the travel website Where Is Your Toothbrush? A non-fiction writer, he is the author of Guerrilla Yardwork: The First-Time Home Owner’s Handbook. Other than travel and writing, his passions include playing ice hockey and juggling projects.

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