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Ultimate Offbeat Guide To Portland, Oregon

Monster donuts and vacuum cleaner museums? Welcome to Portland!

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Created by iamalexbobalex - January 16th 2017

Portland is United State's undisputed Capitol of Weird. From museums dedicated entirely to old ladies' hats to mysterious 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.

Photo of 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!

Tip: If you dare to venture inside (the bar alone is worth it), know that it's cash only.

Photo of 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-sized marble replica of Michelangelo’s Pietà at the very center, known as Our Lady's Grotto.

Tip: Admission is $5, but trust us, take the elevator up to the meditation room. You won't find another view like it in Portland.

3348 SE Belmont, Portland, OR, US

Circa33

To find your way into Circa33, 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 recipes are from as far back as the 1900's, and the speakeasy's cozy atmosphere makes it a great place to stop and grab a drink after a long day of travel adventure.

Tips: This place has two excellent happy hours - the usual early evening affair, and a late-night version after 11PM. Come early and they've got fantastic dining options with some great seating in the hidden alley.

210 NW 11th Ave, Portland, OR, US

Deschutes Brewery Portland Pub

Photo of McMenamins Kennedy School
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5736 NE 33rd Ave, Portland, OR, US

McMenamins Kennedy School

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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.

Tips: You WILL get lost - just follow the posted signs and you'll be fine. The Kennedy School has live music every Thursday night if you feel like taking in some tunes. If you're staying the night, be sure to check out the soaking pool filled with warm salt water, perfect for soothing aches.

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 cat-free and dedicated to delicious food and beverages, and the other is a cat rescue where you can spend some time with the furry adoptable kitties... and who knows maybe give one a forever home.

Tip: Reservations are encouraged, because seriously, everyone loves kittens. Prices are $5 for half an hour, $8 for an hour.

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