orbike bike events portland oregon

Worst Day of the Year Ride 15!


It’s hard to believe it, but the annual Worst Day of the Year Ride is turning 15 this year! The wildly fun wintertime ride takes participants on a journey around the city, in costume, with plenty of tasty treats and hot drinks along the way.

The event starts and ends at the Lucky Labrador Brew Pub and for the most part the route has been the same over all these years. Not that anyone really minded – the roads are mostly low traffic and the crowd was just so much fun. But this year, to celebrate their 15th anniversary, the organizers decided to switch things up a bit.

This year, the Worst Day of the Year Ride takes riders on an adventure to visit cool neighborhoods in Portland and it will travel all the way to the diagonal streets of the Woodlawn neighborhood at the near-north end of Northeast Portland. Here the ride will take a break at HiWheel, a wine and mead making company with a fantastic outdoor patio for summertime relaxation. Since it’s winter, they’re transforming the space into an oasis of rest stop cool for the afternoon.

Other stops along the way include Ecliptic Brewing, Velo Cult Bike Shop + Tavern, and Cornelius Pass Roadhouse (for the challenge route).

View the Routes

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