Regular Events

Here is a listing of rides, walks, and workshops that occur on a regularly basis. While a few of them happen around the same time each year, the exact dates can change. Check the Upcoming Events page for the current schedule.
These rides and walks are open to everyone. Registration is generally not required, but can be for longer rides, camping trips, or workshops. None of my rides are intense, put on your spandex affairs, and should be okay with anyone who rides regularly. Rides and walks are generally not loops but will start and end near public transit.
If you have any specific questions, please get in touch!

Bicycle Rides

  • Palm Tree Ride To get spirits up and prove that winter in Portland isn’t so bad, this ride makes a tour of palm trees and other exotic/tropical/evergreen plants. A different route each year. Generally occurs the 3rd Sunday of January. 
  • Dead Freeways Ride Though Portland is now considered the standard bearer of livability, during the 50’s and 60’s it went through the same highway building stage as every other American city. The watershed event was the defeat of the Mount Hood Freeway in the early 70’s. From that point Portland bucked the trend and concentrated on alternative transportation and liveable neighborhoods. This ride explores the route of this freeway that wasn’t to be along with Harbor Drive, a freeway that is no longer with us, and other ill-fated freeway projects. Occurs every once in a while. 
  • Various History/Geography Rides These rides vary between 5 to 15 miles and are based on a Portland history theme, like Train History, obscure east side cemeteries, the Stark Street Mileposts, or Remnants and Relics of our past. Sometimes (but not always) done in conjunction with a local historian like Dan Haneckow or Doug Decker. At least one ride  a year, if not more.
  • Various Rambles These 10 to 20 mile long meanders are a mix of on and off road surfaces suitable for any bike with at least 35 mm tires. Some climbing may be involved, but you can walk if you need to! They happen sporadically throughout the year.
  • Pizza Ride An expedition exploring Portland’s pizza culture, hitting up about 6 pizzerias in the process. Occurs every year or two, usually in summer.
  • Columbia Gorge Ride An adventure to the spectacular scenery of the Columbia Gorge, just a few hours ride from Portland. Scenic vistas, spectacular waterfalls, and quiet roads! Ranges from a 30 mile out and back, a longer 45 mile option, and an overnight camping option. Occurs usually during Pedalpalooza in June, though not every year.
  • Chehalem Range Ramble A 40-50 mile ride through the hinterlands of Washington County. The route goes over the Chehalem Mountains, a small but steep range with a high point of 1,600 feet. It’s a moderate paced ride with stops, and a mix of paved and unpaved. 35 mm or wider tires recommended. Occurs once a year, either in spring or fall.
  • Sunset/Moonrise Ride A five mile cruise to a mystery destination, one we can watch the sunset and full moon rise! Starts at a spot to pick up food and libations. Occurs about three to five times a year during the summer-ish (read: dry and clear) months.
  • Three Speed Ride This ride series celebrate the humble internally geared three speed bicycle. Several rides happen through the year, from a casual day ride of 10-15 miles, a day tour of 20-40 miles, or an overnight adventure. See the Society of Three Speeds for more details.

Every once in a while (no set schedule)

  • Pedal Potluck Picnic A casual ride 2 to 5 miles (4 to 8 km) in length, each time ending in a unique location. The end destination is a mystery parklike setting where a communal picnic meal is shared. The term “parklike” is used pretty liberally. Sometimes it’s to official city parks that might just be more obscure or out of the way. Or sometimes its to spots that are “park-like”, but hardly fit the definition. Past rides have ended up at traffic circles or wide median strips in the center of a street, some grassy triangles where various streets intersect, and one time picnicked on the well-manicured lawn around a electrical power substation.
  • Alameda Ridge Bicycle Cruise This ride tours the aforementioned geographical anamoly–a short yet steep ridge that cuts a 4 mile diagonal through the relative flatness of Northeast Portland. The ridge features great views and spendy houses, and displays the unique geology of the Northwest while telling the history of Portland’s growth. The ride parallels the Ridge and then ends at Rocky Butte, an extinct volcanic cinder cone that offers a near 360 degree view of the surrounding area. This was the first ride I had done as the Urban Adventure League!
  • Eastside Theater Tour This ride shows off the high concentration of still-operating classic neighborhood cinemas in NE and SE Portland.

Walks/Hikes (happen sporadically)

  • South Portland Expedition An exploration of the South Portland neighborhood, once a vital ethnic enclave, now a distant memory due to highway building. Occurs once in a blue moon. 
  • Council Crest Climb An ascent of Council Crest, Portland’s highest point (1,073 feet/327 metres,) via the Goose Hollow and Portland Heights neighborhoods. Usually occurs once a year.
  • Urban Nature Hike Explorations of nature close to the city and accessible by public transit. Past expeditions have explored the Marquam Nature Trail.
  • Mount Tabor Meander An ascent of Mount Tabor, the eastside’s highest point (650 feet/200 metres) via the not obvious routes. Occurs once a year on average.


  • Bike Touring Workshop A”411″ on self-supported touring, what to bring, what to expect, what to know. Designed for people who regularly cycle, with an emphasis on camping. Occurs several times a year. Most of them cost $15-20, though if there’s one during Pedalpalooza, it’s free with suggested donation. Registration required.

Updated 22 January 2019

3 thoughts on “Regular Events

Add yours

  1. I’d be interested in your Gorge ride or any eastern Oregon trip as well as the bike touring workshop you have. I’m in Albany so I’d want to (gasp!) drive to Pdx! I currently have a Cannondale T-800 and I’m a “senior” citizen who still thinks he’s 45.
    Larry Eckstein

    1. Hello, Larry! Thanks for your interest. Unfortunately after doing two touring workshops already I don’t think another one will happen in 2014. Nothing planned for Eastern Oregon as that’s out of my range. There will be a Columbia Gorge Ride sometime during Pedalpalooza in June, plus some other rides. Stay tuned.

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