Table of Contents:
New York City is known as the Big Apple and Chicago the Windy City, but Portland? Well, Portland is known for being weird. Of course, Portland has plenty of other claims to fame (such as being home to the world’s largest indie bookstore), but its de facto motto “Keep Portland Weird” speaks to its underlying zaniness. Whether you’re a long-time local or a weekend visitor, there are plenty of off-the-beaten-path activities that will help you see Portland from a whole new vantage point. Here are nine of the weirdest, wildest and most wonderful things to do in Portland.
Built in the 1930s as a park ranger station, The Witch’s Castle is a stone structure located in a heavily wooded section of Portland’s Forest Park (which is one of the largest urban forests in the U.S.). After fading into obscurity for years, the deserted two-story building found new life in the 1980s, when local high school students discovered it was the perfect place to throw parties. Today, The Witch’s Castle is covered in moss and graffiti, which makes it look like something out of a Hansel and Gretel storybook. Many hikers now love embarking on a half-mile hike to the castle and snapping photos of the abandoned building.
Dating back to 1879, Huber’s is the oldest restaurant in Portland. From its famous roast turkey to its old-school bar setup, Huber’s has long been recognized as a Portland institution. To get the full experience, make sure to order Spanish Coffee. A server will then come by your table, light a glass of rum and triple sec on fire, and top it off with coffee, coffee liqueur, whipped cream, and just a touch of nutmeg.
One of the best parts of exploring Portland is that you’re bound to stumble across something wacky and weird in the most unexpected of places. Case in point: the Portland Troll Bridge. Take a trip to a historic trestle railway bridge just outside of Portland, and you’ll see a variety of brightly colored trolls (and troll graffiti and paintings) underneath the bridge. There’s no consensus as to exactly when and why these trolls began to pop up, but one thing is clear: it’s a fun place to explore. Don’t forget to bring a troll of your own to add to the growing troll population.
As one of the most popular nude beaches in Portland, Collins Beach is a great hangout spot for anyone who wants to sunbathe, read or relax sans clothes. After soaking up the sunshine, head over to the Collins Beach UFO Boat, a graffiti-covered boat that is shaped like a UFO. Built in the 1970s by a man who was convinced it was the perfect place to weather the end of the world, the boat has long since been abandoned. But if you love stories about abandoned ships, you’re sure to enjoy exploring this colorful boat.
Popular wisdom has long held that breakfast is the most important meal of the day…and it’s hard to think of a better breakfast than a fruit smoothie or acai bowl! If you can’t decide whether to start your morning off with breakfast or a workout, we have good news for you: there’s no need to choose! Instead, you can head to Moberi’s, a bike-powered smoothie shop on a quest to make healthy living accessible to the masses. Customers can pop into one of four locations and pedal a bike that’s hooked up to a smoothie-powered blender to try their hand (or feet, in this case) at making their own smoothie or acai bowl.
If you’re looking for weird things to do in Portland, you won’t want to miss out on Pairings Portland, a quirky wine shop and bar with a never-ending list of themed wine flights and pairings. For example, you could pop in for The Office Wine Flight (which offers five wines reminiscent of characters from the hit TV show) or the Virgo Astrology Wine Flight (which offers five wines paired according to qualities of the astrological sign, as well as tarot pairings). You can even have some of your favorite bottles of wine delivered to your doorstep or sign up to be part of the shop’s wine subscription club.
You may not have had “visit a vacuum museum” on your Portland bingo, but Stark’s Vacuum Museum may make you want to rethink that omission. Established in 1932, Stark’s Vacuums is one of the largest independent vacuum retailers in the U.S. Even if you’re not in the market for a new vacuum, you’ll have fun perusing their main store and museum, which houses “25 of the most iconic and loved vacuums in history.” As you walk through the museum, you’ll see a progression of vacuum cleaners from their early days to today. Best of all, admission is free. Don’t be surprised if you walk away with a sudden desire to do a bit of cleaning when you get home.
Portland is synonymous with breweries, and one of the most original ways to maneuver from one brewery to the next is by bicycle. Grab a few friends and book a trip on BrewCycle, a biking tour of some of the best breweries in the city. Choose from various two-hour, three-stop brewpub crawls where you can pedal from one place to the next and buy beer at each stop. Prices range from $30 to $39 per person, depending on the day.
If you love a good ghost story, why not spend the night in a haunted hotel? Dating back to 1927, The Heathman Hotel has earned a reputation as one of America’s most haunted hotels. Guests report that rooms 703, 803, and 1003 are particularly known for paranormal activity. Don’t be surprised if you notice items moving around the room, see blurry faces, or hear unexpected noises at night.