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9 Most Bizarre Events & Festivals in PDX (Keep Portland Weird)

Every city has a fringe, but Portland maintains an unusually visible odd streak. From a fiercely independent music scene to clowns riding tall bikes and marching bands on stilts, Portland prides itself on its quirky nature. It’s no wonder one of it’s most slogans nicknames is “Keep Portland Weird”.

We’ve compiled our favorite bizarre, legendary, and curious festivals, street fairs, and some fun PDX tours.

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soap box derby Portland, Oregon

Keep Portland Weird: Best Festivals, Tours & Street Fairs

Here are a few of the annual Portland festivals that give the Rose City its unique atmosphere. You can find a lot of weird things to do in Portland; things that make Portland unique and celebrate the city’s diversity. Keep Portland Weird and plan to attend one of these fun festivals in 2023!

The Portland Pirate Festival

Portland Pirate Festival
Photo Credit: Portland Pirate Festival

Every September, in the shadow of the St. Johns Bridge, scurvy buccaneers invade Portland’s beautiful Cathedral Park. Part interactive theater experiment, part country fair, part costume party, the Portland Pirate Festival is reportedly one of the largest pirate gatherings in the world. Wander across the grass and you’ll be accosted by one-eyed men who ask if you’ve seen their treasure hereabouts, and buxom wenches serving up beer from local Rogue Brewery.

Children will get lost in the wonders of Scupper Monkey Island, a playground of bounce castles, face painting, and puppet shows. “Pirate entertainment” casts a wide geographical net, but manifests mostly as indigenous music from around the globe.

Focused on Caribbean and Polynesian music and dance, the festival also features Scottish Highland, Spanish gypsy, and belly dancing performances. But for serious swashbucklers, the cannon demonstrations and sword fighting re-enactments make the weekend. These demonstrations help ground the giddy festivities in historical reality.

Many pirates here take their roles seriously, building a character over several days or even years. But even the most casual marauders wear costumes all weekend. Once a year, Portland’s residents trade in their iPhones for mugs o’ grog and a rousing round of sea shanties.

Pedalpalooza & the Naked Bike Ride

While the city has gained a reputation as bike-friendly, nothing could prepare a visitor for Portland’s two-week paean to the bicycle: Pedalpalooza, a series of 200-plus loosely connected events, all on bikes. Serious racing cyclists will not find much competitive spirit here; Pedalpalooza caters to a casually bike-crazy population that loves to cycle around town in search of fun.

Bikers of every persuasion can participate in these free events. Beginners can take a casual ride through a quiet neighborhood. For the adventurous, bike polo and bike jousting take over the city parks. Garden tours, brewery tours, and scavenger hunts roam the city. At night, mobile dance parties bring the funk by strapping on a boom box.

Pedalpalooza kicks off with the World Naked Bike Ride, a 10k ridden in only birthday suits. Riders must be 18 to participate, but other than that, few rules apply – par for the course in the community-oriented, almost anarchic atmosphere of Pedalpalooza.

Filmed by Bike Festival – May 18-21, 2023

Filmed by bike event
Photo Credit: Filmed by Bike

The 21st Annual Filmed by Bike is May 18-21 at the beautiful, historic Hollywood Theatre in Portland, Oregon. This festival screens bike-centric films from around the world. Other events include bike rides with featured film makers, late night parties and breakfast on several downtown Portland bridges.

The Bloody Mary Festival – June 10, 2023

Hash Kitchen bloody mary in Scottsdale

The Bloody Mary Festival brings together the best Bloody Mary’s made by local bars, restaurants, and craft mixes.

Attendees taste them all before voting for the coveted People’s Choice Award. The Festival is much more than Bloody Marys! Tastes from local food & beverage companies, photo ops, a dancing tomato, and a panel of expert judges add to the day’s festivities. ​ Join this incredible brunch-time party and help crown “The Best Bloody Mary” in Portland! ​

Location: The Redd on Salmon; 831 SE Salmon Street Portland, OR 97214

Sherwood Robin Hood Festival – July 14-15, 2023

A magical festival for all families and attendees of all ages, the 2023 Sherwood Robinhood Summer Festival will be held July 14 and 15.

Experience a unique blend of modern and medieval entertainment at the annual festival in Sherwood, where you can revel like it’s the Dark Ages. This weekend-long event promises fun for the whole family, featuring archery competitions, a Maid Marian court, a castle building contest, a parade, and exciting stage shows.

Portlandia Mermaid Parade & Festival – July 29, 2023

Portlandia Mermaid Parade and Festival
Photo Credit: Portlandia Mermaid Parade and Festival

This year’s Portlandia Mermaid Festival theme is “Black Mermaids Matter,”. This free, family-friendly, inclusive and body-positive event will include a parade, a splash mob dance party, the crowning of the grand marshal and guest speakers.

PDX Adult Soapbox Derby – August 19, 2023

Portland Adult Soap Box Derby

Big kids relive their childhood street-racer dreams each summer in the PDX Adult Soapbox Derby. Mt. Tabor, Portland’s urban volcano, hosts the races. For a day, cars made of recycled windshields and welded metal stream down the hill. Usually, a shady park filled with picnics, joggers, and kissing couples, Mt. Tabor becomes a racetrack for a day. From the sleek to the silly, 39 cars run preliminary heats to advance; three cars ultimately race for the title.

Spectators from the neighborhood and all over Portland come out to watch the races, cheer on their favorite cars, and maybe even witness a crash. Rules are few, but include functional breaks, power by gravity alone, and a horn. Participants should in good faith spend $300 or less on the car, to keep the races to a level where many community members can participate. But the designs are often ingenious, and the Derby organizers encourage invention and creativity.

The Zombiewalk

On a calm morning, as you’re headed to work, sipping your latte, you may notice a zombie staggering down the sidewalk toward you. Or several thousand zombies. Released into the streets, a parade of Frankenstein’s lurches through downtown for a few hours.

While many of Portland’s alternative festivals encourage frequenting the local watering holes, the Zombiewalk is more of an interactive theater performance. Held in late October, the Zombiewalk offers a chance to debut creative Halloween costumes, such as Zombie Sarah Palin and Zombie grandma.

And zombies care. The walk raises money for the Oregon Food Bank. Nothing says “Keep Portland Weird” like a few hundred zombies giving food baskets to the poor out of the goodness of their undead hearts.

Urban Iditarod

Note: The Portland Urban Iditarod has not happened the last 3+ years. Below is the original information for anyone still searching for this event.

The Alaskan Iditarod is one of the most grueling tests of human endurance on the planet – one person and her team of loyal dogs sledding across the vast expanse of frozen tundra. Portland’s version involves a costumed “musher,” enthroned in a shopping cart, being pulled through downtown by four friends.

Over a four-mile course, this race is more fun and only slightly less grueling than the original. Luckily, it also includes multiple rest stops for beer (“watering the dogs”).

Creative costumes abound. Sleds range from Viking ships pulled by Valkyries to nuns pulling Jesus. In 2009, a team of loincloth-clad cavemen pulled a cart of mankind’s first fire, which was actually on fire. Applaud the Alaskan endurance sledders if you like, but running through Portland in a loincloth in March takes true grit.

The Portland Urban Iditarod hardly qualifies as a race, since there are no official winners declared. For safety, actual canines are not invited to participate.

Looking for more of Portland’s quirkiness? Check out this great Keep Portland Weird Website: www.keepportlandweird.com.

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