6 places that give Portland its wonderfully weird reputation

Portland, Oregon

If you don’t happen to be in town for Portland’s annual World Naked Bike Ride, don’t worry—there’s still plenty of weirdness to be found. You may see a bagpipe-playing Darth Vader unicyclist or a moped gang buzzing down the street on any given day. However, if you want to drink the city’s wonderful weirdness in even more deeply, head to these unique destinations. And remember, when it comes to Portland, the weirder, the better.

One beautiful Autumn day in Portland Oregon downtown from Vista Bridge with view of Mount Hood City Skyline and Trees with Fall Color Foliage

Wee park, wee folk 
You might want to think twice about packing a picnic blanket for Mill Ends Park, as it will likely be larger than the park itself. The “World’s Smallest Park,” founded by former local journalist Dick Fagan, takes up just 452 square inches in the middle of Taylor Street. Peek into the foliage and look for Patrick O’Toole, leader of a leprechaun colony said to inhabit the park. Fagan’s column, Mill Ends, chronicled happenings in the tiny terrain before 1969, claiming it as the sole leprechaun colony west of Ireland. Look for a tiny swimming pool, Ferris wheel or other amusements to entertain the tiny folk.

Mixed race girl looking at grass with magnifying glass

Wonderfully weird eats
Having a late-night doughnut craving? Not only is Voodoo Doughnuts open 24/7, but you’re likely to walk in on a midnight doughnut-eating contest or even a wedding. You’ll find about 90 varieties of imaginative doughnut creations amid the whimsical decor, including an enormous sprinkled doughnut on the ceiling (aptly named the Holy Doughnut). Get your sweet-and-savory fix with a bacon-topped maple bar, or savor a sugar rush with a frosting and cereal-coated donut. If you want something a little more unique, try doughnuts in the shape of voodoo dolls, or those that look like recently passed celebrities.

Donut with pink icing and sprinkles on blue background

Weirdest home amusement park
Before descending into the Woodstock Mystery Hole, you must sign a waiver that states: “I, the undersigned, do hereby certify that I must be out of my mind to climb down into a damp, dark hole when I’m perfectly safe where I am.” The hole is but one attraction found in the ample backyard of Barron Mind in the Woodstock neighborhood of Portland. It includes a fun regenerator, a dream boat and other oddities. Call Barron in advance to arrange a tour and he’ll meet you at the mystery gate, which has a unique design rumored to yield only to those who are pure of mind. Climb down a ladder to find yourself among stone walls with mysterious archways and a “Door That’s Never Been Opened.”

Terrible woman getting out the well

Suck it up!
Even if you hate vacuuming, Stark’s Vacuum Museum will put a smile on your face and make you feel better about this household chore. Imagine owning an 1800s Busy Bee vacuum that took two people to operate—the husband would follow his wife around, pumping the hand-operated bellows while she worked the nozzle. Then there’s the surprisingly sturdy Depression-era cardboard vacuum cleaner that still operates. Amazingly, these vacuums work on the same technological principles as the quiet, purring modern models for sale in Stark’s Vacuum Cleaner’s adjacent showroom. Knowledgeable employees are on hand to answer your questions as you browse through the free museum.

Housewife hoovers under the family trying to keep her copy space clean

Shanghai surprise
Back in the 1850s, able-bodied men were known to be kidnapped straight from their seats in Portland bars and forced to serve the rest of their lives at sea. Women and children weren’t exempt either, and were likewise snatched and sold into slavery. Trap doors and secret entrances leading from taverns to the tunnels helped kidnappers carry out the nefarious task. Although most of the Shanghai Tunnels have been filled in thanks to modern construction, you can still tour segments of the tunnels in the basements of local restaurants. Shake off the eerie chill afterwards with a Mushroom Ale at Old Town Pizza.

Worn wood trap door on the floor of the loft of a barn

Kidd’s of yesteryear
Tap into your inner child and explore thousands of toys at Kidd’s Toy Museum. You might not be old enough to remember playing with those from between 1869 and 1939, but there’s plenty to fascinate the modern child too. Mechanical banks are the heartbeat of the multi-room collection—put a coin on an elephant’s trunk and watch it toss it into a slot on its back. You’ll also find a plethora of antique cars, trucks and trains, as well as tin replicas of bygone characters such as Mortimer Snerd. Fair warning: The historic collection contains a sprinkling of toys considered offensive by today’s standards, such as soldiers with open wounds.

Toy Cars of the last century