Weird & Wonderful Things to Do in Portland, OR

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Looking for a Pacific Northwest weekend getaway? Enjoy these weird and wonderful things to do in Portland, Oregon—a destination for craft beer lovers, foodies, outdoor enthusiasts and history buffs.

When to visit Portland, Oregon

If you want to see Rose City in full bloom, visit in summer. You’ll get the best out of Portland’s green spaces and access to the great outdoors during the drier, sunnier months of the year.

July and August are the driest months averaging 17 mm (0.65 in) with temperatures ranging from 14-27 ˚C (58-81 ˚F).

June is a little touch-and-go, but not a bad choice. Rainfall averages at 43 mm (1.7 in) and temperatures range from 12-23 ˚C (54-74 ˚F)

Getting around Portland

Portland is a very compact, walkable city. Even if your legs (or the weather) fail you, the public transport system is easy and affordable.

TriMet manages the city’s public transportation system and you can tap on/off any of their light rail, streetcars or buses with a contactless credit card, Apple Pay, Google Pay or Samsung Pay. If you are staying longer and qualify for reduced fares, you might want to opt for a Hop Fastpass.

As a budgeting guide, an adult fare is $2.50 which will allow you to travel for 2.5 hours. There is also a daily cap of $5. See more on fares, plan your trip or learn more useful information about public transport in Portland here.

Rideshare companies Uber and Lyft operate in Portland, as do carshare programs: Zipcar and Getaround. Last by not least, there is a bike share system called Biketown, which is owned by Lyft and sponsored by Nike.

Unique things to do in Portland OR

People Watch in Portland’s “Living Room”

Pioneer Courthouse Square is sometimes known as Portland’s Living Room. The city square is a local hangout spot with outdoor chess, fountain, amphitheatre and other features. This is a prime people-watching spot, location for public events and holds a lot of history including the former site of the first Oregon public school, established here in 1858.

Portland Art Museum

The Pacific Northwest’s oldest art museum was opened in 1892 in Portland. The Art Museum holds a collection of over 42,000 pieces stretching through Native American art to contemporary works. The space includes two connected buildings with an outdoor sculpture park. See opening hours and admission here.

Lan Su Chinese Garden

Located in the Old Town Chinatown area, these Chinese-style gardens are reputed for their authenticity. Portland’s sister city is Suzhou in Jiangsu Province China, a region known for its Ming Dynasty Gardens. Lan Su is a collaboration between the cities and was built by Chinese artisans from Suzhou. By the way, Lan Su roughly translates to “garden of the awakening orchids”—isn’t that beautiful?! Find out more including which plants are currently in bloom by visiting the official website.

Get lost in Powell’s City of Books

Powell’s City of Books is considered the world’s largest independent bookstore. Bookworms will delight in almost a million books to choose from. Powell’s also hosts regular readings and book signings by authors so check the events page on their website. Make sure you leave some room in your suitcase for all your purchases.

Wander Tom McCall Waterfront Park

Tracing the Willamette River, Tom McCall Waterfront Park is an easy stroll with a number of attractions. From here, it’s easy to see how Portland got the nickname “Bridge City”. Following the Waterfront Park Trail from north to south you’ll come across:

• The Japanese American Historical Plaza which blooms with cherry blossoms each spring.
• View of the Portland “White Stag Sign”, although the view of the sign is actually better from the Burnside Bridge.
• The Battleship Oregon Memorial and Oregon Maritime Museum.
• Mill Ends Park (further explained below) is off to the side in the centre of the Parkway.
• A fountain dubbed Salmon Street Springs.

Visit the world’s smallest park

Effectively a glorified median strip on Naito Parkway, the world’s smallest city park was recognised by the Guinness Book of Records in 1971. The tiny greenspace of 60.96cm (24in) diameter was created by a local journalist whose office overlooked a neglected hole in which he planted flowers.

He had the spot officially designated a park by the City in 1948. His justification: snail races and a leprechaun colony that only he could see—he was of Irish heritage and it was St Patrick’s Day after all! (You can get the full story here.) A sight for those who like quirky attractions, but not one to go out of your way for.

Get a glimpse of Portlandia

The United States’ second-largest copper repoussé statue after the Statue of Liberty is “Portlandia”, a beautiful female figure clasping a trident. The sculpture, inspired by the Portland City Seal, was commissioned by the City in the 1980s. Why have you never heard of it? The sculptor, Raymond Kaskey, holds the reigns on the statue’s copyright and diligently pursues anyone who uses it without authorisation. Head down to the Portland Building at 1120 SW 5th Avenue to gaze up at the goddess.

Tip: Portlandia is not where it is marked on Google Maps. It is the correct building but the opposite side. See my pin on the map below for the correct location.

Learn the lore of the Shanghai Tunnels

Tour the underground portals that lie dormant beneath Portland’s Old Chinatown. A remnant of late 19^th century-early 20^th century, these supposed catacombs are rumoured to have been used for all things nefarious from opium dens to kidnapping. Local lore tells of boozy men being abducted and enslaved as crew aboard ships to Asia. This practice is called crimping though you might know it by the nickname Shanghaiing, given the boats’ destination was often China.

There isn’t much to back these stories up, but don’t let a shortage of archaeological evidence get in the way of a good story! You can only visit the Tunnels on a guided tour. You’ll get more value out of the entertainment and storytelling than you will out of anything you might actually see. After touring Seattle’s underground, I gave this one a miss.

Eat your way through PSU Farmers Market

If you’re around on a Saturday morning, enjoy a wander through the Portland Farmers Market at Portland State University (PSU). The year-round markets take place in the South Park Blocks. Vendors include fresh produce, meat, cheese, baked goods, flowers, food carts and more. There is also live music and chef demonstrations that run June-October. Check the Portland Farmers Market website for seasonal hours and more details.

Tip: Go hungry and eat your way around the market. Great food includes Xian Bing from Great Tang and sweet works of art at Mio’s Delectables.

Smell the Roses in Washington Park

Washington Park encompasses a number of attractions including Oregon Zoo and the World Forestry Center. Two must-see highlights are the International Rose Test Garden (seasonal) and Portland Japanese Garden:

International Rose Test Garden

Summer visitors to Portland will enjoy the International Rose Test Garden comprised of around 10,000 rose bushes covering 650 varieties. Established during WWI, this Garden is where hybridists in Europe would send new roses to be tested. The annual bloom takes place May through October and the Test Garden is free to enter, so it can get quite crowded.

Portland Japanese Garden

Next up in Washington Park is the Portland Japanese Garden. Conceived in the late 1950s and opening in 1967, the Japanese Garden was intended as a symbol of peace and to provide Portlanders with a beautiful green space. The Garden has since evolved and expanded with increasing popularity. It includes the Kashintei Tea House and a Cultural Village. You might even find yourself there in time for an Ikebana tutorial or tea ceremony demonstration – check their event page for the schedule.

The 5.5-acre Garden does not receive any funding from the city and therefore an entry will set you back a fee of USD18.95. For more details including opening hours, see the Portland Japanese Garden website.

Find the “Witch’s Castle” in Macleay Park

Next on our list of premier Portland green spaces is Macleay Park, which is the southernmost end of much larger Forest Park. No list of things to do in Portland OR is complete without mentioning a hike to Stonehouse, known colloquially as “Witch’s Castle”. Really, it’s an abandoned homemade popular by some spray paint-wielding teenagers.

The home formerly belonged Danford Balch and his family in 1850. Danford hired Mortimer Stump Well to help him clear some land and his new employee fell in love with Danford’s teenage daughter Anna. Danford wasn’t happy about the arrangement, so the couple ran off and eloped. When they next came in contact with Anna’s father, he shot Mortimer in the head and was later hanged for the murder of his son-in-law.

Danford’s widow Mary Jane continued to live in the home. Later it served a variety of purposes including a park ranger station and restroom for hikers until it was eventually damaged by a storm and abandoned altogether. The “Witch’s Castle” lies a 0.8km (0.5mi) hike from the Upper Macleay parking lot.

Tip: Get a ride to Pittock Mansion Viewpoint and then hike the Wildwood Trail down to Stonehouse. It’s 2.9 km (1.8 mi), about 40 mins walk, mostly downhill.

Tour Pittock Mansion

Near to Macleay Park, you’ll find the sweeping views and French Renaissance-style charm of Pittock Mansion. The National Register of Historic Places-listed home was constructed between 1912 and 1914 for newspaper mogul, businessman and adventurer Henry Pittock. The 23-room sandstone château stands on a prominent hilltop with outstanding vistas of Portland, the Willamette River and Cascade Mountains.

Tour the 23-room sandstone château for a look back in time. The interiors have been curated to authentically represent the era, and include artwork and furniture from the collection of its original owners and their Portland contemporaries. See the Pittock Mansion’s official website for more details including admission fees and seasonal opening hours.

Note: If historic homes aren’t your thing or you’re on a budget, you can enjoy the scenery from Pittock Mansion Park Viewpoint without paying to enter the Mansion.

Explore Alberta Arts District

A short drive from the city and you will find the Alberta Arts District with plenty of street art, fun boutiques, quirky bars and cafes to explore.

Places to eat, drink and be merry

Here are the places that we ate, drank and loved in Portland with a few additional recommendations that we were given but didn’t have enough time to try out.

Lu Lac Vietnamese Kitchen – This place gets really busy and it is easy to taste why. Go early or order takeout.

AFURI Ramen + Dumpling – Delicious ramen and dumplings with excellent cocktails. This restaurant utilizes a kiosk ordering system which can be slow, but once you’ve ordered the food arrives fast.

Eleni’s Philoxenia – Greek fine dining. Book in advance for this popular little spot in the Pearl District.

World Foods – An international supermarket with a great coffee bar and amazing deli of Mediterranean foods (it’s owned by a Lebanese family). Excellent place to pick up a picnic. We bought a selection to take on the train ride back to Seattle.

Multnomah Whiskey Library – Make sure you book or are prepared for a long wait. We missed out, but the Maître d told us that Sunday is the best day for walk-ins should you forget to make a reservation in advance.

Voodoo Doughnuts – A Portland institution but beware of the long line to get in and go early.

5^th Ave Pod (Food Trucks) – Many of the food trucks seemed to be closed at the moment, so we didn’t get a chance to try them but in my research, the 5^th Avenue pod seemed to garner the most recommendations.

Case Study Coffee – Great coffee in the Albert Arts District.

Ecliptic Brewing – A fun brewpub in the Mississippi District with great food.

Map of Things to do in Portland

Enjoy your time exploring Rose City!

Peace, love & inspiring travel,

Madam ZoZo