9 Biking Daycations in Portland, Oregon


Does the scene above look familiar? That's me on my phone at VeloCult, one of the best bike shops because they serve beer and you can actually talk to fellow bike lovers, yet here I am looking for places to eat. So, I am just as guilty. What happened to the art of wandering or roaming? Many of us grew up in a pre-technology environment where we enjoyed walking into the woods or hopping on our bike and getting lost, yet it's so hard to trust our instincts.

Disconnecting from the internets, and in turn, being alone with your thoughts or talking to a real human being makes you happy. In places with no wifi or cell reception, I have a better time and the surprise adventures are a rush of dopamine that social media can't touch.

And thus, I invite you to first check out 9 treasure troves of Portland, disconnect, get lost and talk to people along the way.

In Town

These 6 Portland city experiences are sure to give you a happy belly and soul.

Blue Star's blueberry, bourbon, basil donut

Blue Star's blueberry, bourbon, basil donut

1. Donuts. Is there anything they can't do?

The donut scene in Portland is a force to be reckoned with, and we figure the calories burned on even a shorter urban ride will justify at least one extra donut.

Donuts of Portland

  1. Tour - Downtown Coffee, Donuts  & Delights by Third Wave Coffee Tours

  2. Self-guided tour - The World of Portland Doughnuts, Mapped (Eater.com)

Japanese Garden moss, aka forest carpet

Japanese Garden moss, aka forest carpet

2. The Great <Urban> Outdoors

See the most beautiful outdoor spaces Portland has to offer; tea houses, koi ponds, countless varieties of roses, and rambling paths under soaring trees. We usually find zoos a little depressing, but this one is done very well.

Green spaces:

  1. Japanese Garden
  2. Rose Garden,
  3. Washington Park
  4. Forest Park
  5. Zoo

Pro Tip - Avoid sweat and take the MAX red/blue line up the hill to the zoo and bike down from there. Make sure to bike around the south side of the Rose Garden on the trail to the south that links up with the MAC Trail downhill.

Eastbank Esplanade

Eastbank Esplanade

3. Bridges over Willamette

There's no better way to see the Willamette River by bike than to explore the many different bridges that cross it, and the waterfront paths that follow it through town.

bridges & riverside trails

  1. Tilikum Crossing
  2. Morrison Bridge
  3. Hawthorne Bridge
  4. Eastbank Esplanade
  5. Waterfront Park Trail
  6. Willamette River Greenway Trail
  7. Broadway Bridge
  8. Steel Bridge
Hair of the Dog Brewery is good and they have a giant bike corral out front.

Hair of the Dog Brewery is good and they have a giant bike corral out front.

4. So Much Beer, So Little Time

There are more breweries and beer-showcasing venues in Portland than anyone could ever fully explore... and what a wonderful problem to have. Let the experts help you home in on the best of them.


  1. Hop in the Saddle - $9.95 for book that will take you on 5 self-guided bike tours of the 30-40 best craft beers in Portland
  2. Beercycling - $1475/person for a 5 day, beer centric bike tour from Portland through the Columbia River Gorge, aka waterfall alley.
  3. Brew Cycle - $25/person for group, pedal powered trolley
  4. Cycle Portland - $39+ for beer tour
  5. Pedal Bike Tours - $59+ per person for Oregon Brewery tour
Harrison Street Neighborhood Greenway

Harrison Street Neighborhood Greenway

5. Won't You be my Neighbor?

Portland's neighborhoods are overflowing with the little things that make cities truly livable: independent retail, killer food that isn't pretentious, and well-loved, funky, beautiful houses. Make sure to follow the neighborhood greenways for super chill riding with house gawking opportunities.


  1. Mississippi
  2. Alberta
  3. Vancouver/Williams
  4. MLK
  5. Hawthorne

neighborhood Greenways

  1. Going
  2. Concord
  3. Harrison/Lincoln
  4. Salmon/Taylor
El Pilon food cart off of 2nd and Pine streets

El Pilon food cart off of 2nd and Pine streets

6. Food. one Day is not enough.

Unless you've been to Portland recently, you probably don't realize just how good their food is. Wide ranges of cultures are embraced here, and those with dietary concerns will find menus and servers that are ready for them. We're also pretty sure the "food truck" concept was invented here.


  1. Cycle Portland - $39+ for foodie tour
  2. Everybody's Bike Rentals & Tours - $59+ for "Tastes & Treasures" tour
  3. Gluten Free Graze by Bike - $95/person includes Brompton bike rental, 2 beer/cider tastings and 3 food tastings and 5 hour tour by Bikabout's founder, Megan Ramey
  4. Pedal Bike Tours - $59+ per person for "Food Cart" tour

favorite food

Teote, Mi Mero Mole, El Pilon food cart, Bamboo Sushi, Toro Bravo, Tasty-n-Sons, Por Que No

Around Town

These 3 experiences around Portland are less than 1 hour drive or shuttle ride away from downtown and will leave you feeling like you stepped into a Tolkien novel.

Wachlella Falls

Wachlella Falls

7. Waterfall Alley

Boasting an unbelievable density of waterfalls, the Columbia River Gorge is an easy reach by car or shuttle from Portland and you will feel like you've traveled hundreds of miles from any big city. 

Rides, transportation & Parking

  • 3-14 miles one way (shuttle, $5 roundtrip) - take the Columbia Gorge Express between Gateway in Portland and Multnomah Falls and bike eastward as far as you want to go. Shuttle operates Friday through Sunday (and federal holidays), May 26 through Sept. 24 in 2017. "Each bus can accommodate up to three bikes in the luggage compartment under the vehicle." 
  • 31 miles one way (requires driving)- For those up for a challenge, park your car at the Troutdale Gorge Hub (next to the old train depot) and ride the Historic Columbia River Highway to Thunder Island Brewing in Cascade Locks. You'll pass every major waterfall.
  • 46 miles one way - for the hard core, bike directly from Portland to Cascade Locks. We hear that Thunder Island Brewing lets people camp in their back yard, if you're up for bike camping.

DISCLAIMER - due to the very sad Eagle Creek fire in September of 2017, much of the Historic Columbia River Highway that connects the waterfalls, and the trails to the waterfalls are closed. These photos were taken the week before the teenagers tossed smoke bombs that ignited the fire and we feel so lucky to have experienced "the before". Refer to Trip Check for interstate closure updates and Oregon State Parks for park closure status.

Oneonta Gorge

Oneonta Gorge

Twin Tunnels on the Historic Columbia River Highway Trail

Twin Tunnels on the Historic Columbia River Highway Trail

8. America's 1st Scenic Highway

One of the best sections of the Historic Columbia River Highway to bike is the car-free 8 mile segment connecting the small towns of Hood River and Mosier, Oregon. Expect stunning views, twin tunnels, and lots of beverage tasting.

Itinerary & Route Map

Getting There

  • By Train 🚆 : take Amtrak's Empire Builder daily service from Union Station in downtown Portland to Bingen, WA. This line accommodates folding bikes only (no boxed bike service). Once in Bingen, call the Hood River taxi (541) 399-9954 or engage in social normalized hitchhiking across the Hood River bridge.
  • By Shuttle: CAT Transit, $8 one way. Tuesday and Thursday only service from Portland Art Museum or Gateway to Hood River or The Dalles. Accommodates 2 bikes, first come, first serve on front bike rack
Columbia Gorge at sunrise

Columbia Gorge at sunrise

The Narrows swimming hole in the Clackamas River

The Narrows swimming hole in the Clackamas River

9. Epic Swimming Holes & Hot Springs

The perks of an active volcanic landscape include waterfalls, emerald green glacial meltwater, swimming holes tucked away in quiet corners, and natural hot springs. 

Itinerary & Route Map

We are partial to the Cascading Rivers Scenic Bikeway, 30 miles from Portland, which includes a couple swimming holes and a couple hot springs opportunities.

Lagoon at Kingfisher Campground

Lagoon at Kingfisher Campground