Ultimate Offbeat Guide To Portland, Oregon

High schools converted into hotels, monster donuts, and vacuum cleaner museums? You guessed it, you're in Portland!

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Created by anncontella - April 30th 2016

Portland is United State's undisputed Capitol of Weird. From museums dedicated entirely to old ladies' hats, to underground Shanghai tunnels, it's hard to go anywhere in Portland without stumbling across an offbeat travel gem, and lucky for you, we've got the best ones collected right here.

Strip Club Shaped like a Jug
4.0

7427 NE Sandy Blvd, Portland, OR, US

Strip Club Shaped like a Jug

Even if strip clubs aren't your thing, you can at least appreciate the weirdness that is Pirate's Cove. Located at 74th Sandy St, this Portland Landmark has been a must-see spot for the last 80 years! Known as the most friendly strip club in the state, the Pirate's Cove is, in fact, shaped like a giant rum bottle. Yar!

The Grotto
4.8

8840 NE Skidmore (NE 85th and Sandy Blvd), Portland, OR, US

The Grotto

From strip clubs to Catholic shrines? You must be in Portland! The Grotto is one of the city's most visited churches, and for good reason. The 62-acre shrine is a beautiful refuge for any weary traveler. At the very heart of the peaceful shrine is a rock-cliff with a life-size marble replica of Michelangelo’s Pietà at the very center, known as Our Lady's Grotto.

2916 NE Broadway, Portland, OR, US

Things From Another World

Owned and operated by the creators of Dark Horse Comics, Things from Another World is basically Disney Land for comic book lovers. Serving the nerdy since 1979, Things From Another World has one of the most extensive collections of comics, superhero paraphernalia, and rare collectibles imaginable, and it's all in one place. You won't leave empty handed, promise!

Slappy Cakes
4.1

4246 Se Belmont St, Vancouver, WA, US

Slappy Cakes

Not only was Slappy Cakes named one of America's top ten destinations by the Food Network, it's also one of the most fun (and delicious) breakfast eateries in the city of weird. Slappy Cakes puts the customer to work, and the result is your own handmade breakfast masterpiece. Waiters deliver everything from pancake batter to all the fixings, and you cook your breakfast on your table's very own built-in grille. It's a perfect spot for the culinary control freak!

Circa33
3.7

3348 SE Belmont Ave, Portland, OR, US

Circa33

To find your way into this famous Portland speakeasy you'll have to discover the secret bookshelves. The bar features an array of mouth-watering cocktails, all of which cover the best years in mixology history. The drinks range from 1900s style and on, and its cozy atmosphere makes it a great place to stop and grab a drink after a long day of travel adventure.

The Hat Museum
4.4

1928 SE Ladd Ave, Portland, OR, US

The Hat Museum

You can't go to Portland without visiting a few unique museums, and The Hat Museum is just that. With collections that range anywhere from novelty, retro, vintage and international, The Hat Museum has one of the most intensive collections of head-gear accessories in the country. You don't even need to be a hat-nerd to appreciate the fashionable collection. One of the most popular exhibits is the 1910 Craftsman-style, which is home to vintage Nurse's caps, deerstalkers (aka Sherlock Holme's hat), to retro Stetsons.

Jupiter Hotel
3.5

800 E Burnside St, Portland, OR, US

Jupiter Hotel

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The Jupiter Hotel is marketed as Portland's "young and hip" lodging, which definitely comes across when you notice there are complimentary condoms in your room. The rooms are cozy, the decor is quirky.

Be sure to grab dinner at the Doug Fir, an attached restaurant with a great Twin Peaks-inspired Pacific Northwest lumberjack vibe.

The streetcar is just a few short blocks away, and plenty or restaurants are within walking distance.

107 NE Grand Ave, Portland, OR, US

Starks Vacuum Museum

Not only has Starks been selling people vacuums since 1932, they also own and curate the Starks Vacuum Museum. The walls of the museum are completely covered with over 300 different vacuums that range anywhere from the 1800s, to that space-age cleaner your grandmother used to own in the 1960s.

Kidd Toy Museum
4.4

1327 SE Grand Ave, Portland, OR, US

Kidd Toy Museum

Mr. Frank Kidd was a lifetime collector in the field of children's toys. His obsession started off with vehicular toys, and eventually grew into The Kidd Toy Museum.

Today the museum is home to hundreds of still banks, planes, character toys, badges, railroad locks, and even early Oregon memorabilia, and that's just the tip of the iceberg. The toys range anywhere from 1869 to 1939, and are pretty much guaranteed to grab anyone's curiosity.

Mill Ends Park
4.2

Southwest Front Avenue and Taylor Street, Portland, OR, US

Mill Ends Park

Is it any surprise that something as quirky as the world's smallest park is in Portland, Oregon? The little recreational area known as Mill Ends Park is a miniscule 452 inches square, and it's located on SW Naito Parkway's median strip. Unfortunately, there's enough room in the park for just one visitor at a time.

The tiny little park first sprouted up in 1948-- it was originally intended to be the site of a light pole, but when the pole didn't arrive, the hole dug for it became overgrown with weeds. On St. Patrick's Day in 1948, Reporter Dick Fagan held an official dedication for his new park, which he called "Mill Ends", home of a leprechaun named Patrick O'Toole.

The Dinner Detective, Portland
3.0

550 SW Oak St, Portland, OR, US

The Dinner Detective, Portland

Dinner theater doesn't always have to be bad. Take the Dinner Detective Murder Mystery Dinner Show, for instance. You've got four courses to figure out who done it, while a group of actors try to pull the wool over your eyes. Half of the time the guests are seated with actors and they don't even know it. Top sleuth leaves with prizes and bragging rights, and for the cost of a dinner and a movie, it's totally worth it.

Cargo Imports
4.5

81 SE Yamhill St, Portland, OR, US

Cargo Imports

If you're looking for a place to drop some cash then look no further. Cargo Imports isn't just an antique store, it's mixture between an art gallery and retail warehouse, where importers from around the world put their uncommon objects on display.

The Pearl District store is stocked floor-to-ceiling with folk art, furniture, jewelry, and pretty much any treasure your heart could desire. Just be prepared to leave with a lighter wallet.

Moberi
4.7

1755 NW 23rd Ave, Portland, OR, US

Moberi

Moberi is the Original Bike Powered Smoothie Bar where the bikes literally powers the blenders. What's better than grabbing a protein shake on a busy day? Blending your own on one of Moberi's man-powered bike blenders! Not only are the shakes delicious, you're guaranteed to get a great workout while you're at it.

Freakybuttrue Peculiarium
3.6

2234 NW Thurman St, Portland, OR, US

Freakybuttrue Peculiarium

No offbeat road trip to the land of the weird would be complete without a stop at The Freakybuttrue Peculiarium. Not only do they have a a 10-foot tall Bigfoot, zombie brain, interactive alien autopsy, and Bugeaters Delight Sundaes, sprinkled with dried mealworms and scorpions on top, but if you can down the whole thing in one sitting you're a club member for life! Oh yeah, and did I mention that admission is free?

McMenamins Kennedy School
4.1

5736 NE 33rd Ave, Portland, OR, US

McMenamins Kennedy School

The Kennedy Elementary School opened in 1915, and after years as a fully-functioning school, it was bought and converted into one of the coolest hotels in the country. With 57 awesome guest rooms, many of which still have their original chalkboards, water fountains, and desks, guests can spend a week relaxing without ever having to leave the building.

Purrington’s Cat Lounge
3.5

3529 Ne Martin Luther King Jr Blvd, Portland, OR, US

Purrington’s Cat Lounge

Cats and people go together like coffee and cream, which might explain why cat cafes have become all the rage. One half of the Purrington's Cat Lounge is dedicated to delicious (cat free) food and beverages, and the other is a cat rescue where you can spend some time with the furry adoptables, and who knows maybe give one a forever home.

22 SW 3rd Ave, Portland, OR, US

Voodoo Doughnut

Voodoo Donuts is world-famous. If you love the deep-fried desert, than there's a very good chance you're familiar with the bright pink box of sugary goodness. It's not uncommon for the lineup at Voodoo Doughnut to be wrapped around the block, so expect to wait for a bit before you get your grub. Either way, it's totally worth it!

Shanghai Tunnels
3.5

120 NW Third Avenue, Portland, OR, US

Shanghai Tunnels

The Shanghai Tunnels are rumored to be the most haunted place in America.The basement tunnels were an underground network used by some not-so-nice kidnappers known as shanghaiiers. Often times, people will report hearing the sounds of screaming or moaning coming from the darkness, and even children crying. Tours of the tunnels are sure to terrify!

Now that you're prepared, your trip to Portland is guaranteed to be as weird as possible, which lets be honest, isn't hard when you're in Portland.