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This Summer’s Best Bike Outings in Portland

Posted on August 14, 2024   |   Updated on September 30, 2025
City Cast Portland staff

City Cast Portland staff

bike in background. Jenna in foreground in a dress.

Picnic by bike at The Bluffs. (Holden Regnier)

City Cast

How To Plan the Perfect Summer Bike Outing

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Summer is Portland’s best biking season. And Jenna Phillips, who shares her cycling adventures on TikTok as Jenna Bikes, has some picks for the best outings in-town and outside city limits.

In-Town Adventures

If you’re looking for something easy and fun, these are some in-town options:

It’s an easy ride to Mocks Crest Park, in North Portland, for a sunset picnic. “It feels very cool when you approach the park and you see how many Portlanders are just sitting there,” Jenna says.

Bike route: You can approach along Skidmore. And there is also the Failing Street Bridge, over I-5. “There's little, like, zigzags, you have to bike up and down, which is kind of fun, but it's a dedicated pedestrian/bike-only bridge over I-5.”

You can bike to a swim for another easy, in-town outing. Duckworth Dock on Eastbank Esplanade has a weekly summer swim right now. “It definitely feels like Portland's hottest club is the Duckworth Dock on Wednesday evening,” says Jenna. “That's the vibe you get when you pull up on your bike.”

Bike route: Eastbank Esplanade is for pedestrians and bikes only!

Trips Beyond City Limits

If you’re ready to bike a ways, here are two options:

This is another ride to a swimming spot. The park is on the Clackamas River in Gladstone. “There's bathrooms, running water, and there's also kind of this rock area where you can jump in the Clackamas River, which is also awesome on a hot day after biking,” says Jenna.

Bike route: Take the Springwater Trolley Trail from downtown all the way to Gladstone. It’s about 13 miles.

Bonus: Stop at Oaks Park on the way back for a sweet treat.

selfies of two people holding soft-serve ice cream

Sugarpine drive through but on bikes. (Jenna Phillips)

This outing is for the ice cream, but the path also offers some incredible views. “My preferred route is to go straight north until you get to Marine Drive, which is also a lovely place to bike,” says Jenna. “It takes you along the Columbia River, mostly a separated path, which is really beautiful. And my favorite thing about biking on Marine Drive is getting to see planes land and take off.”

Bike route: Marine Drive to Troutdale is some 18 miles, but it’s flat.

Want More Summer Biking?

  • Bike Summer / Pedapalooza still has daily group rides through the end of the month.
  • The last Sunday Parkways is in Southwest Portland next month. The City Cast Portland team will be there too, so come say hello!

Also: Check out more tips for planning a summer bike outing.

The Springwater Corridor Is Boring?

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