Portland, Oregon is the city of craft beer, artisan donuts, and hipsters. It has great shopping, awesome food, and quirky cultural attractions. Portland has been called many things… quirky, weird, and unique all seem to describe it! I’ve been to Portland twice and had such a good time – there are so many fun and different places to check out. This guide will walk you through some of the top unique and weird things to do in Portland, Oregon!
Before we get into all the weird things to do in Portland, let’s talk a bit about the city. Portland is the largest city in Oregon with a population of around 645,000. It’s located in the North of the state, bordering Washington state with the city of Vancouver, Washington just across the Columbia River. Portland is known as the “City of Roses” because of its ideal climate for the flower – warm, dry summers and cool, rainy winters!
Portland is also known for its commitment to being eco-friendly and has a vibrant art, theatre, and music scene. The city is also famous for its many, many breweries and coffee shops, each one totally different and unique! It’s known to be a bit quirky and a bit odd, but that’s what we all love about it! All the unique and cool things to do in Portland are what make it something special. I mean, they even have a sign that says “Keep Portland Weird!”
Unique Weird things to do in Portland
Visit the Creepy Witch’s Castle
This weird attraction in Portland is located in Forest Park and takes a short hike to get to. You can park in the Upper Macleay parking lot (Audubon Society) and walk for about 15 minutes along the well-maintained bath. The hike itself is beautiful, but the endpoint is what makes it all worth it!
The Witch’s Castle is an old, moss-covered stone house right in the middle of the forest. It has a lot of folklore surrounding it, telling the tale of a family in the 1850s who settled into the area. There was a love triangle, a murder, and now apparently two ghosts who haunt the property! Whatever the true story is, it’s one of the most unique things to do in Portland!
Check out the Collins Beach UFO
Sorry to disappoint, but no, it’s not a real UFO! This attraction is actually an abandoned, graffitied boat that is in the shape of something a bit like a UFO. It’s a cool destination to check out while visiting Collins Beach. You’ll need to take the trail from Collins Beach after parking at 2nd or 3rd entrance. Depending on the time of day, the UFO is sometimes only accessible by walking through the water. Keep your eyes open, because it can be hard to spot nestled into the trees.
Hang out at the tiniest park in the world
Mill Ends “Park” has been dubbed by the Guinness Book of Records as the World’s Smallest Park – it’s only 452 square inches! It’s located in the median strip along SW Naito Parkway in downtown Portland and consists of exactly one tree.
While there’s not much room to hang out in this park, that doesn’t stop the city from decorating it according to different seasons and events like Christmas. It’s a super quirky spot in Portland, so make a detour to stop by and grab a pic!
Make friends with the Alpacas
Have you ever seen an alpaca? They are just so fluffy and cute! Very huggable, and very much the weird, out-of-place kind of animal you might expect to see in Portland. The Marquam Hill Ranch is located 37 miles south of Portland, so makes for a good afternoon outing.
At the ranch, you can take a tour and learn more about these amazing animals. You might even be able to feed some! They have a great on-site gift shop with fine goods made from alpaca wool.
Check out the Street Art
One of the best things to do in Portland is to just wander around and look out for street art! And in Portland, there’s no shortage of interesting murals and paintings around the streets. I always find it fun to point out the weirdest or most unique pieces of street art and just have fun taking some pictures and exploring!
Wander through the Freakybuttrue Peculiarium
There is no other word than “weird” to describe this place – definitely deserving of its spot on this “weird things to do in Portland” list! The Peculiarium is full of random and interesting collectibles from creepy dolls to aliens to sci-fi memorabilia… the list goes on. Admission is $5 USD, so definitely well worth a stop at the Freakybuttrue Peculiarium on your Portland adventure!
Catch a show at the Funhouse Lounge
It’s always fun to catch a live show when you are exploring a new city, and the Funhouse Lounge is just the place to go in Portland. They describe themselves as “theatre without the safety net” and have even been voted one of Portland’s Weirdest Bars.
You will be able to catch shows ranging from burlesque, improv, karaoke, plays, storytelling, and so much more. Every show is unique at the Funhouse Lounge, so make sure to check out what is currently on!
Check out the Shanghai Tunnels
If you’re interested in learning more about the sinister past of Portland, including crime, scandals, and dubious characters, you can check out this walking tour of Underground Portland. It will take you through the physical underground of Old Town and Chinatown. You’ll get a guide to tell you all about the different myths and legends of the “Shanghai Tunnels.” The price is $23 USD for the tour.
Portland is home to some excellent shopping. There is Powell’s, the infamous bookstore that’s absolutely worth a visit, but there are tons of weird and quirky shops as well. Some places to check out include Curiosities Vintage Mall (antiques, vintage items), Paxton Gate (taxidermy, animal specimens, seashells, etc.), or Hippo Hardware (quirky home furnishings).
There is so much more to explore, so just get out there and wander a bit! Try checking out the Alberta Arts District or the Pear District for neighborhoods that are easy to walk with lots of cool shopping.
Make a wish at the Wishing Tree
At the corner of Northeast Morris Street and 7th Avenue stands the Wishing Tree, a large chestnut tree covered in paper notes hung all over the branches. It has thousands of people’s wishes hanging there, from long-lost love to wishes for their families to wishes for the world. Blank tags are available for you to go and add your own wish! You never know, it might just come true!
Discover Last Thursday on Alberta Street
Portland is known as an arts and culture hub, and there is no better display of this than the Last Thursday street experience that takes place – you guessed it – on the last Thursday of every month. Alberta Street opens up to local artists and gallery exhibits, musicians and dancers, or other types of performers. It is free to attend and you can take part in this vibrant arts scene!
Catch a movie… In school!
The Kennedy School Theatre is probably the most unique and weird movie theater experience – it’s in an old, converted elementary school! The Kennedy School was an elementary school that opened in 1915 but was converted into a hotel and other attractions in Portland by the McMenamins company. Now, it’s one of the most unique things to do in Portland! They show movies for just $5 USD and are outfitted with comfy old couches and have a bar on-site where you can grab a drink to go with your movie!
Best time to visit Portland
The best time to visit Portland, Oregon is during the Spring, Summer, and Fall months, roughly between May to September. This is the season where it is likely to be dry and warm. While it can get hot in the summer, it is never as hot as many other parts of the US and maintains that generally moderate climate like much of the Pacific Northwest.
The winter months can also be enjoyable in Portland, and you may strike some deals since it’s tourist off-season, but be prepared for rain. If you have a lot of indoor activities lined up (of which there are lots to do in Portland!) it can still be enjoyable and the temperature is mild.
How to move around Portland
A lot of people love that Portland is a big enough city to have tons to see and do, but it is small enough that it has a community, small-town vibe. Being fairly small, it is easy to move around Portland. There are a few different options to navigate through the city.
Driving in Portland is no big deal – traffic is minimal and it’s easy to navigate and get around. There are lots of parking lots in the downtown core and they’re reasonably priced at around $2/hour.
Biking is part of every Portlanders identity, it seems! It’s one of the most popular ways to get around, and it’s no wonder why – Portland is rated America’s most bikeable city! Biketown is a popular and easy-to-use bike rental service, available all around the city.
This is such a fun way to get around the city! Portland has a few rent-a-scooter services, like Bird or Lime, where you can use an app to unlock a scooter to use and then return it to a series of drop-points around the city. It’s a really easy way to get around and explore and is definitely one of the cool things to do in Portland!
The downtown area of Portland is quite small and easily walkable. Because it’s a very eco-friendly city, walking is encouraged – there is even a no-cars-allowed bridge that went up over the river in 2015 to encourage car-free transportation!
Portland has a good system of public buses, in addition to the MAX train system and the Portland Streetcar. The prices are cheap at $2.50/2.5 hours or $5/day.
Uber and Lyft are both available in the city and offer a relatively cheap and easy way to get to all the different attractions in Portland. Traditional taxis are also plentiful around the city.
Where to eat in Portland (unique places)
There are a lot of amazing places to eat in Portland, no doubt about it. I even took home a magnet as a souvenir that says “my Portland souvenir” pointing to a full belly! You can really find anything in this city, and they are especially famous for vegan or plant-based food, unique and quirky restaurants, and lots and lots of craft beer and coffee shops!
Here are some of the unique places you can check out to grab some food and drink
Join a food tour
One of the best ways to check out all the unique and off-the-beaten-track places to eat is through a food tour. A food tour will take you with a local guide to some places you might not find yourself! Popular and highly-rated tour companies include Lost Plate and Eat Adventures Food Tours. A food tour is also a great way to explore a new area and make some new friends, as they usually take around 3-4 hours to complete.
Check out the food truck pod
A quintessential Portland experience is eating at one of the many, many food trucks around the city. Food trucks are cheaper than eating out at a restaurant and also have their own fun, quirky vibe. I think the best place to go in the city is the 5th Avenue Food Truck Pod, which is an area where at least 20+ food trucks gather and offer their food. It’s cool to check out different trucks, and perhaps sample a few things from multiple trucks!
The legendary Voodoo Doughnuts
Voodoo Doughnut is one of the most famous attractions in Portland and if you don’t go there on a trip to Portland, did you even go?! But, in all seriousness, it’s definitely worth a visit! Voodoo has two locations in Portland and they are known for their crazy and unique flavors (horchata, the ring of fire, or voodoo doll are just some of the interesting ones!) and wild and wacky store décor. There is usually a line out the door, but it is so worth the wait!
Portland has a bunch of other donut shops, too, so make a “donut crawl” out of it and check out Blue Star Donuts, Doe Donuts, or Heavenly Donuts, among the many choices!
Try something new at Salt & Straw
This is no ordinary ice cream shop! Salt & Straw is an artisan ice cream store that creates some of the most amazing and unique flavors. It’s very popular with locals and visitors alike – I stood in line for an hour, but it was so worth it! They have a ton of unique flavors that you’ve never tried before, such as Goat Cheese Marionberry Habanero, Arbequina Olive Oil, and Pear & Blue Cheese. I promise it will be an ice cream experience like no other!
Another fun and unique place to check out while in Portland is the Farmers Market. There are multiple markets around the city, with some open year-round. It’s a great place to pick up local, fresh food and produce in addition to checking out local artists for handmade wares and crafts.
Visit a Cat Café
Portland is known for its many amazing coffee shops – one on each corner it seems! But perhaps the most unique experience is the Purrington’s Cat Lounge! Not only can you go and grab a coffee, but you can hang out with the adoptable cats that hang out in the café. They partner with cat adoption services in the city to provide safe and smooth transitions for guests who want to take home a new furry friend! Purrington’s cat lounge is temporarily close but planning to open soon. Check their website for further information.
Play Games while you eat!
One of the most fun and innovative things you can do in Portland is going to a full-blown board game café! So, while you’re eating delicious food and grabbing a drink, you can hang out with some friends and play popular board games like Settlers of Catan or the classic Monopoly. There are a few of these cafés around the city such as Mox Boarding House or Senet Game Bar, which has a full-service restaurant.
Where to stay in Portland
In a city as unique and interesting as Portland, you know there’s also a bunch of cool places to stay! I have personally stayed in Airbnbs and hostels during my trips to Portland and enjoyed both of them. Depending on what you’re looking for, there are some great options.
Portland is not a huge city, but there are still some unique neighborhoods and areas you might want to check out, depending on what you’re looking for during your stay in Portland!
- Downtown Portland: Great option if you have never been before and want to do all the touristy areas
- Pearl District: Perfect if you love coffee shops, restaurants, and shopping!
- Alberta Arts District: The best choice if you are an art-lover and enjoy gluten-free and vegan food.
- Nob Hill: Located close to Forest Park, this is a good choice for people looking for something a little quieter and close to the park to enjoy the green space.
Airbnbs and vacation rentals
I think Airbnb is one of the best ways to explore a new city and get to know some of the local charms, or in Portland’s case, weirdness. You can choose a neighborhood that might appeal to you (i.e., Alberta district for something artsy) and then carefully look at the reviews and options available on Airbnb for something that fits your style!
There are tons of boutique hotels in Portland, so you don’t have to default to a boring chain hotel during your stay. I already mentioned the Kennedy School Hotel (a converted school) as a quirky option to stay while in Portland.
Some other popular options, if you’re looking for a hotel with some character, are The Jupiter Hotel (boutique hotel and live music venue), Caravan (a tiny house hotel), or Ace Hotel (classic hipster hotel with vintage furniture and turntables).
If you’re on a budget while visiting Portland, you might opt for a hostel as a cheaper option. I stayed in the HI Portland Northwest Hostel and really enjoyed it. It was clean and had everything you need, including some complimentary craft beer tasting! There are other hostels throughout Portland, too, so it’s a good option for something budget-friendly.
Portland, Oregon is an amazing city with a reputation for being different and unique. Between the crazy museums, fascinating shops, and unique places to eat and drink, I think you’ll agree that there are tons of weird things to do in Portland!
I’ve always enjoyed my trips to Portland and recommend you take your time to just move slow, explore, and enjoy all the different things to see and do. Make sure you go with an empty suitcase and stomach because, I can assure you, both will be full by the end of your trip. Enjoy your time in Portland!
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Alyssa is a freelance writer with her Bachelor of Arts in International Studies degree. Alyssa is passionate about travel and has been to over 20 countries – and counting! Living in Vancouver, Canada, she loves to take advantage of the mountains and ocean by getting outdoors as much as possible. When she’s not writing, Alyssa is probably walking by the river, caring for her many houseplants, or grabbing a coffee with a friend. You can keep up with her on her personal blog.