Keeping Portland weird: why this is one of America’s quirkiest destinations

updated 12.02.2019

Introduced in 2003 as an initiative to support local businesses, “Keep Portland Weird” has fast become Portland’s unofficial motto. Anyone who’s been to the city or watched cult TV show Portlandia will know that the phrase has been taken to heart, and Portland is proud to be, well, a little bit quirky. Here’s why we think it’s one of America’s strangest but greatest cities.

1. It’s home to the world’s smallest park
2. The city takes cycling to extremes
3. There’s a selection of strange festivals
4. The museums are somewhat unusual
5. There are haunted tunnels running under the city
6. A clown-themed bar is one of many memorable places to drink
7. Chocolate lovers rejoice: there’s a 21ft-tall chocolate waterfall
8. Portland has the only vertical street in North America
9. Portland Timbers’ mascot is a real lumberman with a chainsaw
10. You can get hitched in a doughnut shop

1. It’s home to the world’s smallest park

Guinness world record-holder Mills End Park is just two feet across. Barely larger than a plant pot, the world’s smallest park is difficult to spot – walk along the waterfront and you’re likely to see bemused visitors near SW Taylor Street trying to match the park on their map with the area around them.

Despite its size, it’s treated like any other park – events and concerts take place around the site (including, apparently, a wedding), and a miniature ferris wheel was once placed into it by a full-size crane.

2. The city takes cycling to extremes

A whole host of bizarre bicycle-themed events are held throughout the year in Portland. Every June sees hundreds of people gather in the nude for the World Naked Bike Ride, which may sound silly, but is for a serious cause: to raise awareness for cyclists’ vulnerability on the roads.

If you’re not up for riding in the buff, there’s the Worst Day Of The Year bike ride to help you get over the February blues (fancy dress encouraged), and a bike-themed film festival in May.

You can take organised cycling tours with Pedal Bike Tours, all of which end up back at their shop where you can talk bikes over a local beer.

3. There’s a selection of strange festivals

As well as the bike film festival, there’s the Faux Film Festival, which parodies the film industry, creating fake trailers, spoofs, mockumentaries and more.

If you’re into music, head over for the KK Quiet Music Festival: a weekend of “sonic serenity” for those who prefer to turn down the bass.

4. The museums are somewhat unusual

A wheelchair-bound zombie greets you outside The Freakybuttrue Peculiarium and Museum, which is home to a creepy collection of oddities, such as blood-splattered rooms and a bath filled with what looks like human organs. Dogs and “decent costumes” get in free, but it’s not for the fainthearted.

For those without a strong stomach, the Stark Vacuum Museum houses, you guessed it, a bemusing selection of vacuum cleaners. It's a wonder no one ever thought of this before.

5. There are haunted tunnels running under the city

The basements of many downtown bars and hotels in Portland link to the Willamette River via underground passages. Running under Chinatown and Old Town, the so-called Shanghai Tunnels are said to be haunted by the ghosts of workmen snatched from the passages and sold to shipmen.

You can sign up to an underground tour of the tunnels to discover more about Portland’s potentially shady past, and whether you believe in the supernatural or not, the setting is certainly ghostly.

6. A clown-themed bar is one of many memorable places to drink

The Funhouse Lounge is filled with unnerving images of clowns, including a grinning head that sits as the centrepiece of a corner table. It's all your childhood nightmares come true.

Get your caffeine fix at Rimsky-Korsakoffee House and you're also likely to get more than you bargained for, as some of the cafe’s “bewitched” tables vibrate or move up and down. The dimly-lit interior, filled with hanging ornaments, adds to the haunting atmosphere, and don’t miss the bathroom; its bizarre underwater theme features a mannequin in a kayak and feet dangling from the ceiling.

7. Chocolate lovers rejoice: there’s a 21ft-tall chocolate waterfall

Visit Candy Basket’s Portland shop to witness chocolate cascading down a 21ft marble and bronze waterfall. Just don’t do an Augustus Gloop and taste it – the chocolate is likely to have been rotating for a while. Instead, try some of the confectioners’ hand-crafted treats, or take a tour of the factory.