21 Weird, Unique, and Fun Things To Do In Portland Oregon
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Portland, Oregon’s largest city, has long had a reputation for being, shall we say…weird. That’s no insult, either. Portlandiers wear that badge with pride.
That weirdness the city is known for brings in tourists by the millions, annually. Recently, those millions included the two of us.
We visited a number of tourist attractions and local favorites during our visit in order to bring to you, dear reader, our list of twenty-one weird, unique, and fun things to do in Portland.
Some of these include links to their own, detailed posts we typed up. So if you’d like further information on that particular one, give that link a tap (psst, doing so also helps support this site. Thanks in advance).
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A Quick Note About Portland…
It’s no secret. Portland has been in the news a lot recently and you’ve no doubt noticed.
Between the protests, homelessness, and crime, its been never ending.
For prospective, we stayed, ate, and walked around downtown Portland. Not once did we feel threatened and no one ever bothered us.
That said, there are homeless camps everywhere and crimes such as theft and vehicle break-ins are common.
Much like any city you visit, be aware of your surroundings and keep your valuables close by. You shouldn’t have a problem.
That being said, let’s get on with the list!
1) Voodoo Doughnuts
Much like you can’t visit Seattle without hearing about Amazon or Starbucks, chances are good that if you’re coming to Portland, someone will mention Voodoo Doughnuts.
They’re not the best doughnuts in the city (in our humble opinions), but they’re delicious and certainly the best at making creative, unique doughy treats.
A few of our favorites include the Bacon Maple Bar, Dirt, The Homer, Vicious Hibiscus, Maple Blazer Blunt, and the Voodoo Doll (their signature donut).
They have a couple locations but for the true experience, head to the Old Town store. This is the original location.
Get there early to avoid the line (it gets long). We arrived around nine and were able to walk right in but during the tourist season, that rarely happens.
They also accept online orders and offer delivery through DoorDash and Uber Eats if you don’t want to make the trip to the store.
2) Funhouse Lounge
Catching a comedy show at the Funhouse Lounge is one of those quintessential Portland experiences you must do.
They offer a variety of shows such as comedy musical parodies, stand-up comedy, improv, amateur nights, burlesque, and more.
They also have a clown room you can check out while you’re there. Unfortunately for us, it was being used as a storage room at that time, so we couldn’t see it.
The show we came for, however, was hilarious! It was a musical parody of the classic film, Pulp Fiction. The actors and actresses were superb.
To see their current schedule and purchase tickets, check out their website.
3) Mill Ends Park
This one definitely falls under the “weird” category of this article. Mill Ends Park is a tiny (and we mean, TINY) urban park in the middle of the street near an intersection.
With a total area of just 452 square inches in a two-foot circle, Mill Ends Park is likely the smallest park you’ll see anywhere in the world.
There’s only room to safely fit two to four people, max. So if there’s a group already there, hang out on the sidewalk until they’re done.
It is located near the intersection of SW Taylor and S Naito PKWY and can be easily accessed from the Tom McCall Waterfront Park (near the fountain).
4) The Freakybuttrue Peculiarium and Museum
Unfortunately, we ran out of time and couldn’t visit this awesomely weird place, but you definitely should!
This museum is packed with creepy exhibits, merchandise, and artwork. Per their website, it isn’t recommended for small children.
For further information, you can check out their website here.
5) Witch’s Castle
Witch’s Castle was one of the highlights for us. Not just because we got to explore the ruins of this local favorite, but because the hike on the way was stunning!
Located in the boundaries of Forest Park, the hike to Witch’s Castle (or Stone House) begins at either the Upper or Lower Macleay Park along the Wildwood Trail.
It’s a short, half-mile hike from the upper trail or a near equally short 3/4 mile hike from the lower trail to Witch’s Castle.
The lower portion of the trail was closed during our visit, so I can’t speak on what it’s like. The upper portion, however, is stunning.
If you’re in Portland and you’re even remotely into hiking, you need to check this one out. For more detailed information, read our guide here.
6) Pioneer Courthouse Square
Long known as, “Portland’s Living Room”, Pioneer Courthouse Square is a 40,000 square-foot public space in the center of Downtown Portland.
When there’s not a pandemic going on, the city holds many local events and concerts here. It also features a few local food trucks and a Starbucks.
Even when there isn’t an event going on, it’s still worth checking out. There’s plenty of artistic exhibits to see and during the holidays, the city Christmas Tree is on full display.
7) Wishing Tree
Since 2013, tourists and locals alike have been writing their wishes on little white tabs and hanging them from this special tree.
It’s located on the corner of NE Morris street and 7th avenue on private property. The owner of the property keeps blank tabs on the tree. Simply pick one and write down your wish.
8) McMenamins Kennedy School
Kennedy School was originally built in 1915 and served as a public elementary school until 1975. It closed and remained vacant for years.
The McMenamins brothers, who were the founder’s of Oregon’s first post-prohibition brewpub, purchased the property and began restoring it in 1997, saving it from demolishment.
A lot of effort was made to preserve the building and its contents, such as; using school book pages as wallpaper, framing yearbook photos, and painting murals of former students.
These days, what was old is now new again as Kennedy School retains much of its original charm. In the former classrooms, you can now find bars, restaurants, lodging, shops, and more!
To get information on room rates and more, check out their website here.
9) Pittock Mansion
Pronounced, Pit-tick, this beautiful home was where Henry and Georgina Pittock lived in the early 1900’s. Henry Pittock was the owner of the newspaper, The Oregonian, and is often credited as the man who built Portland.
Georgina found her way to Portland along the Oregon Trail and would go on to find success in founding numerous charities and organizations such as Ladies Relief Society and Women’s Union.
The family would occupy the mansion until 1958, when the Grandsons of Henry and Georgina would put it up for sale. It sat empty for years and was heavily damaged by storms.
After holding fundraisers, the city would eventually acquire the property and restore it. Today, self-guided tours are offered to the public.
To purchase tickets or for more information, go here.
10) Portland Japanese Garden
Once dubbed by former Ambassador of Japan, Nobuo Matsunaga, as, “the most beautiful and authentic Japanese garden in the world outside of Japan”, the Portland Japanese Garden is a can't-miss destination.
Unfortunately, we were rained out on this day and couldn’t go (expensive cameras and water don’t mix). To see pictures of this beautiful place, head over to their website here.
11) Eat Gourmet S’mores at ‘1927 S’mores Company’
Remember sitting around the campfire and enjoying that sweet, chocolaty classic, S’more? Well, you can now enjoy one in a downtown setting as well.
Located on SW Alder street in Downtown Portland, 1927 S’Mores Company serves up amazing gourmet s’mores and hot chocolate.
In our travels, this is the first time we’ve encountered a place solely dedicated to s’mores, so we felt it deserved a spot on this list.
Be sure to get there early, as the interior isn’t spacious at all. You can view their Yelp profile here.
12) Powell’s Books
Powell’s Books is the largest independent bookstore in the world. It has served Portland since 1971 and is beloved by locals and tourists alike.
The store has multiple entrances, several levels (with elevators), and has over one million books for sale. You can find just about any book you could think of here.
The original, flagship location can be found on W Burnside street in the downtown area. If you’d like to browse their inventory online, you can do so here.
13) The ‘Keep Portland Weird’ Mural
Remember at the beginning of this article when I stated, “Portlandiers consider their weirdness as a badge of honor”? Here’s the proof.
It’s one of the many murals found throughout the city, but it’s special because it represents the city’s quirky nature and the individualism of its citizens.
It’s painted on the back of Dante’s Nightclub in Old Town, right across the street from VooDoo Doughnuts (making it an easy two-for-one trip).
The exact address is 350 West Burnside street.
14) The Redwoods at Hoyt Arboretum
This is another one we got rained out on and wish we had more time to explore. This short loop trail starts near Hoyt Arboretum and goes through a beautiful forest of redwood trees.
You can find it in Washington Park, not too far from the Japanese Garden and Portland Zoo.
15) Cartlandia
Since Kisha is a natural-born foodie, us coming here was a no-brainer. With over 30 food trucks to choose from, Cartlandia is every foodie’s dream come true.
It is located on SW 82nd avenue and is open daily from 7am to 9pm. Covered seating is plentiful and on-site parking, while limited, is available.
Here, you can find just about every category of food, including; BBQ, Mexican, Asian, Egyptian, breakfast, desert, and so much more.
For up-to-date information on which carts are currently on site, check out their website here.
16) White Stag Sign
This one is more for the Photographers out there (unless you happen to enjoy staring at signs in the middle of the night).
You could always photograph or see the sign during the day but at night, when it’s all lit up, is best, in our opinion.
The sign is viewable from the waterfront, but it is partially obstructed by trees. To get the best view, head up to the Burnside Bridge.
Either side results in a great photo but in my opinion, I liked the left side of the bridge (facing the sign) the best. This area can be a bit sketchy a night. So if you go, be cautious.
17) Tom McCall Waterfront Park
While you’re nearby checking out White Stag, be sure to spend some time exploring Tom McCall Waterfront Park.
It runs adjacent to the Williamette River and is around 36 acres in size. You’ll get amazing views of Portland’s many bridges and see many art installations along the way.
Cherry Blossom Trees dot the walking path and are a special treat for the eyes if you get here while they’re in full bloom.
18) Mount Tabor Park
Located just a short drive from the downtown area, Mount Tabor Park is a large forested park covering what was once an active volcano!
It has hiking trails, tennis courts, playgrounds, and amazing 360-degree views of the city and surrounding landscapes.
19) The Portlandia Statue
The Portlandia is a sculpture by Raymond Kaskey. It’s easy to find as it’s right along the sidewalk and above the entrance of the Portland Building on SW 5th avenue.
The sculpture was commissioned by the city in 1985, is 34-feet high, weighs 6.5 tons, and is based on the Portland city seal.
It is located just a few blocks away from Pioneer Courthouse Square, making it an easy jaunt once you’re done exploring that.
To get photos form an elevated position, head over to the building across the street and go up the escalator.
As it’s private property, I asked a Security Guard if it was ok and he let me go in. So keep that in mind if you decide to do the same.
20) Discover Art Murals
Portland, including and especially the downtown area, is littered with amazing art murals on the sides and rear of buildings and walls.
21) Chase ALL The Waterfalls
While you won’t find any in the city itself (aside from the few cascades in Forest Park), you’ll find a whole bunch of them just outside of it.
Just around 30-minutes or so up the Columbia River Gorge Scenic Byway is where you’ll find the majority of them.
A few of the most popular ones include Multnomah Falls (the tallest waterfall in Oregon), Bridal Veil Falls, Elowah Falls, Latourell Falls, Wahkeena Falls, and so much more!
List Recap:
VooDoo Doughnuts
Funhouse Lounge
Mill Ends Park
The Freakybuttrue Peculiarium and Museum
Witches Castle
Pioneer Courthouse Square
The Wishing Tree
McMenamins Kennedy School
Pittock Mansion
Portland Japanese Garden
1927 S’mores Company
Powell’s Books
The ‘Keep Portland Weird’ Mural
The Redwoods at Hoyt Arboretum
Cartlandia
White Stag Sign
Tom McCall Waterfront Park
Mount Tabor Park
Portlandia Statue
Art Murals
Chase Waterfalls
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