Featured Trips Types:

  • All Featured Trips
  • Scenic Drives
  • Outdoor Escapes
  • Family Road Trips
  • Movie Filming Locations
  • 48 Hour City Guides
  • Classic USA Road Trips
  • National Parks Trips & Tips
  • Weird Guides
  • Interstate Highway Exit Guides
  • Ghost Guides
  • Full Metal History
  • Plan Your Island Escape to Georgia's Golden Isles
Clear All

Accommodation Types:

  • All Accommodation
  • Bed and Breakfasts & Inns
  • Boutique Hotels
  • Holiday Inn
  • Hostels
  • Hotels
  • Motels
  • Unique Stays

FastBook

Look for FastBook for quick links to
your favorite booking sites

Clear All

Attractions & Culture Types:

  • All Attractions & Culture
  • Amusement Parks
  • Children's Attractions
  • Fall Attractions
  • Museums
  • Offbeat Attractions
  • Top Attractions
  • Tours & Excursions
  • Winter Attractions
  • Zoos & Aquariums
Viator
Look for the icon to book the best
tours and activities nearby.
Clear All

Food & Drink Types:

  • All Food & Drink
  • Bars & Drinks
  • Burgers & BBQ
  • Coffee & Tea
  • Delis & Bakeries
  • Diners & Breakfast Spots
  • Ice Cream & Sweets
  • Restaurants
  • Vegetarian & Health Food
  • Wineries, Breweries & Distilleries
Clear All

Outdoors & Recreation Types:

  • All Outdoors & Recreation
  • Beaches
  • Fall Foliage
  • Geographical Areas
  • Geographical Features
  • National Parks
  • Nature Reserves
  • Parks & Gardens
  • Scenic Point
  • Swimming Spots
  • Trails & Hikes
Clear All

Points of Interest Types:

  • All Points of Interest
  • Abandoned
  • Architecture
  • College Icons
  • Film & TV
  • Historic
  • Holiday Lights
  • Literature
  • Military
  • Monuments
  • Photo Op
  • Planes, Trains, Autos
  • Public Art
  • Science & Tech
  • Spooky Places
Clear All

Vacation Rentals Types:

  • All Vacation Rentals
  • HomeAway
  • Vacation Rentals

We’ve partnered with HomeAway to find you the perfect vacation rental.

Clear All

Camping & RV Types:

  • All Camping & RV
  • Cottages & Cabins
  • KOA Campgrounds
  • RV Parks
  • Tent Campgrounds
Clear All

Entertainment & Nightlife Types:

  • All Entertainment & Nightlife
  • Art Galleries
  • Casinos & Gaming
  • Cinemas
  • Games & Amusements
  • Music
  • Nightlife
  • Shows & Entertainment
  • Theaters
Clear All

Services Types:

  • All Services
  • ATMs
  • Auto Services
  • Gas/Fuel Stations
  • Rest Areas
  • Tourist Information
  • Transportation
  • Vehicle Rental
Clear All

Shopping Types:

  • All Shopping
  • Antiques
  • Books & Music
  • Crafts & Handmade
  • General Goods
  • Gifts & Souvenirs
  • Groceries
  • Malls & Shopping Areas
  • Quirky Shops
  • Thrift & Flea
Clear All

Sports Types:

  • All Sports
  • Adventure Sports
  • Cycling
  • Equestrian Sports
  • Fishing & Hunting
  • Golf
  • Gyms & Fitness
  • Skate & Surf Spots
  • Stadiums
  • Water Sports
  • Winter Sports
Clear All

Motoring Types:

  • All Motoring
  • Automotive Attractions
  • Off-Road Trails
  • Racetracks
  • Scenic Drives
Clear All
  • Trip
  • Places I've Been
  • My Saved Places
  • Collection
  • Featured Trips
  • Accommodation
  • Attractions & Culture
  • Food & Drink
  • Outdoors & Recreation
  • Points of Interest
  • Vacation Rentals
  • Camping & RV
  • Entertainment & Nightlife
  • Services
  • Shopping
  • Sports
  • Motoring
  • DON'T FORGET TO SAVE YOUR TRIP. CLICK HERE.

0 Layers

Ultimate Offbeat Guide To Portland, Oregon

Monster donuts and vacuum cleaner museums? Welcome to Portland!

  • 18
Take This Trip

Created by Roadtrippers - March 30th 2016

Portland is the United States' 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.

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.

The Grotto
4.6

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.

Things From Another World
3.7

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 Disneyland 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.

Tip: If you can manage it, visit on a Wednesday - new comic book day - and it's basically a party.

Slappy Cakes
4.3

4246 SE Belmont St, Portland, OR, 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 this famously weird (and foodie-obsessed) city. Slappy Cakes puts the customer to work, and the result is your own handmade breakfast masterpiece. Waiters deliver everything from pancake batter to the fixings, and you cook your breakfast on your table's very own built-in grill. It's a perfect spot for the culinary control freak!

Tips: Try the chicken-fried bacon. It'll probably knock a year off your lifespan, but man, it's worth it. During the week, you should be able to get a table nice and quick, but on the weekends, expect to wait about half an hour for a party of two.

Circa33
4.4

3348 SE Belmont Ave, 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.

The Hat Museum
4.0

1928 SE Ladd Ave, Portland, OR, US

The Hat Museum

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 collection of hats, which is home to vintage Nurse's caps, deerstalkers (the kind of hat Sherlock Holmes wears) and retro Stetsons.

Tip: Thanks to some funky ticket pricing, the Hat Museum is best seen with a group. It'll run you $75 for a group of 1-6, so the more people you can wrangle, the cheaper the overall cost.

Jupiter Hotel
3.5

800 E Burnside St, Portland, OR, US

Jupiter Hotel

FastBook
$$

Click to find a
great deal for this hotel

The Jupiter Hotel is marketed as Portland's "young and hip" lodging. The rooms are cozy, but the decor is quirky.

Tips: Be sure to grab dinner at the Doug Fir, an attached restaurant with a great Twin Peaks-inspired, Pacific Northwest-lumberjack vibe. Plus, the streetcar is just a few short blocks away, and plenty of other great 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 19th century models to that space-age cleaner your grandmother used to own in the 1960s.

Tip: The Vacuum Museum is located inside an actual vacuum shop, so don't get scared off if a salesman approaches you. Just tell him what you're looking for and he'll point the way.

Kidd Toy Museum
4.6

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 come from as far back as 1869, and are pretty much guaranteed to grab anyone's curiosity.

Tip: You can't beat the price of the Kidd Toy Museum - it's FREE! Their only request is that you sign their guestbook.

Mill Ends Park
4.2

899 SW Naito Pkwy, 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 minuscule 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"... he also claimed that it's home to 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 whodunnit 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.

Tips: The tickets can seem a bit pricy (roughly $150 for two tickets), but you'll get dinner, desert, and a show out of the deal, which puts the total price tag at just under the cost of night at the movies capped off with a nice dinner. The whole experience lasts about three hours... but sorry kids, due to the nature of the show, no one under fifteen is admitted.

Cargo Imports
4.0

81 SE Yamhill St, Portland, OR, US

Cargo Imports

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

Tip: Adding to the magical charm of Cargo Imports is their staff palm reader, just in case you need your fortune read while you browse.

Moberi
4.7

1515 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.

Tips: Don't worry, if you don't want to pedal for your smoothie, they're happy to do it for you. Parking can get tight at this location, but you shouldn't have a problem a block or two down in any direction.

Freakybuttrue Peculiarium
3.9

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 10-foot tall Bigfoot, a zombie brain, and an interactive alien autopsy, they also serve up Bugeaters Delight Sundaes with dried mealworms and scorpions on top. Sounds gross, but if you can down the whole thing in one sitting you're a club member for life!

Tip: Admission is FREE! Be sure to browse the collection of oddities for sale: most of them were locally made!

McMenamins Kennedy School
4.5

5736 NE 33rd Ave, Portland, OR, US

McMenamins Kennedy School

FastBook
$$

Click to find a
great deal for this hotel

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.

Purrington’s Cat Lounge
3.0

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.

22 SW 3rd Ave, Portland, OR, US

Voodoo Doughnut

Voodoo Donuts is world-famous. If you're a fan of donuts, then there's a very good chance you're familiar with this bakery's bright pink box of sugary goodness.

Tips: It's not uncommon for the line at Voodoo Doughnut to wrap around the block, so expect to wait for a bit before you get your grub. It's worth it, though.

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 alleged 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!

Tip: If you have respiratory issues, you might want to avoid - this tour puts you down in the dusty tunnels below the city for nearly two hours. Expect to spend about $15 bucks a person.

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.

Roadtrippers

The best of Roadtrippers - hand picked by our team!