Portland Tweed Ride
Annual Portland ride where cyclists don tweed, vintage outfits, and period attire for a stylish pedal through the city. Prizes, a tweed library, and genuine sartorial flair.
The vibe
Tweed, vintage flair, open road
Portland has a lot of themed rides, but the Tweed Ride occupies its own lane entirely. Once a year, riders dust off their vintage outfits, pull out the tweed jackets and flat caps, and set off on a ride that feels less like exercise and more like a rolling costume party for cycling enthusiasts with a taste for the old-fashioned.
The 2026 event starts at Revolution Hall on SE Stark at noon on May 3rd. There’s a tweed library on-site for anyone who wants to borrow something appropriate for the occasion, plus prizes from sponsors for the best-dressed. The pace is social, the atmosphere is convivial, and you don’t need a vintage bike — though it certainly helps the look.
It’s not free, but it’s one of those events where the ticket price buys you something you wouldn’t have experienced otherwise. If you own even one piece of tweed clothing, this is the ride to wear it to.