There’s a certain magic to discovering a city from the saddle of a bicycle. The pace is just right—slow enough to catch the scent of a coffee roaster on the breeze, yet fast enough to feel the urban landscape unfold around you.
And there is no city in America more suited to this kind of discovery than Portland, Oregon.
As the capstone to my journey along the Oregon Trail, exploring this city on two wheels felt like the perfect modern conclusion to an epic historical trek.
Portland isn’t just bike-friendly; it’s a cyclist’s paradise, boasting over 350 miles of dedicated bike infrastructure that weaves through its vibrant neighborhoods.
But this guide is more than just a series of maps. It’s a curated journey designed to show you the city as I saw it, blending the must-see sights with the quirky history and hidden stories that make Portland truly special.
We’ll cover the practicalities, but we’ll also dive into the tales of car-free bridges, extinct volcanoes in city parks, and the best local spots to refuel.
Planning Your Portland Bike Tour: Know Before You Go
This section is designed to get you rolling with confidence. A little preparation ensures you can focus on the fun part: the ride itself.
Renting a Bike in Portland: Your Steed for the City
Finding the right bike is easy in Portland. For a classic, no-fuss experience, the city’s official bike-share program, BIKETOWN, offers bright orange bikes that can be rented from stations all over the city.
If you prefer a more personalized fit or a specific type of bike, several local shops offer excellent rentals and friendly advice.
- Cycle Portland is a popular choice, known for its well-maintained bikes and knowledgeable staff who can offer great local recommendations.  Â
- Everybody’s Bike Rentals & Tours lives up to its name with a huge selection of over 100 unique vintage and modern bikes, ensuring there’s a perfect fit for everyone. They provide a helmet, lock, and lights with every rental, so you can be as safe as possible.
Understanding Portland’s Bike Infrastructure: Navigating Like a Local
Portland’s commitment to cycling is evident in its infrastructure. You’ll encounter a few key terms:
- Neighborhood Greenways: These are low-traffic residential streets where cyclists and pedestrians have priority. They are the backbone of the city’s network, offering a calm and safe way to travel.
- Protected Bike Lanes: You’ll find these on busier streets, providing a physical barrier between you and car traffic.
- Vera Katz Eastbank Esplanade: This iconic path runs along the east side of the Willamette River and even includes a unique 1,200-foot floating walkway, one of the longest of its kind in the world.
Essential Gear & Safety Tips
Portland weather can be unpredictable, so layers are your best friend. A light rain jacket is always a good idea.
Be sure to carry water, and don’t forget your helmet. Traveller reviews consistently praise tour guides who prioritize safety, so take a cue from the pros: ride predictably, use hand signals, and be aware of your surroundings.
Route 1: The Classic Waterfront Loop – Portland’s Essential Ride (11 Miles, Easy)
This is the quintessential Portland ride. It’s an 11-mile, mostly flat loop that showcases the city’s stunning bridges and waterfront parks, making it perfect for a leisurely afternoon.Â
The Route & Logistics
Distance: 11 miles
Terrain: Mostly flat, paved paths
Highlights: Tilikum Crossing, USS Blueback Submarine, Vera Katz Eastbank Esplanade, Steel Bridge, Hawthorne Bridge.
Bald Hiker’s Highlights & Quirky History
This ride is a journey through Portland’s engineering marvels and hidden history.
Tilikum Crossing: Start your ride by crossing this elegant, cable-stayed bridge. Its name, “Bridge of the People,” is fitting, as it’s the only major bridge in the U.S. designed exclusively for light rail, buses, cyclists, and pedestrians—no private cars allowed.
USS Blueback Submarine: As you pedal along the east bank, you’ll spot an unexpected sight: a Cold War-era submarine moored outside the Oregon Museum of Science and Industry (OMSI).
The USS Blueback is a fascinating piece of history, now resting peacefully in the Willamette River.  Â
The Bridges: The loop takes you under and over some of the city’s most famous bridges. The Steel Bridge is a marvel of efficiency—a double-decker, vertical-lift bridge that is the only one of its kind in the world.
Further south, the Hawthorne Bridge is the oldest operating vertical-lift bridge in the country and a workhorse for the city’s cyclists.
Route 2: Southeast Portland – Arts, Brews, and a Volcano (6-10 Miles, Easy to Moderate)
This route takes you into the heart of Portland’s famously eclectic east side, a place of vibrant street art, historic neighborhoods, and a park with a geological secret.
The Route & Logistics
Distance: 6-10 miles, depending on detours
Terrain:Â Mostly flat with a significant climb up Mt. TaborÂ
Highlights: Ladd’s Addition, Mt. Tabor Park, Hawthorne and Division Streets, craft breweries.
Bald Hiker’s Highlights & Quirky History
Ladd’s Addition: Begin by getting lost (in a good way) in the unique, non-rectangular street grid of Ladd’s Addition. This historic neighborhood, with its four diamond-shaped rose gardens and grand old homes, feels like a tranquil escape from the city.
Mt. Tabor Park: From Ladd’s, you’ll begin the gentle climb up Mt. Tabor. The reward for your effort is the incredible fact that you’re standing on an extinct volcanic cinder cone within city limits. The panoramic view of the city skyline from the top is one of the best you’ll find.
Hawthorne & Division Streets: Coasting back down from the park, immerse yourself in the vibrant energy of these iconic streets. This is the epicenter of “Keep Portland Weird,” lined with vintage shops, independent theaters, and sprawling food cart pods that offer a world of culinary delights.
Brewery Stop: Portland is a craft beer mecca. Park your bike at a local favorite like Lucky Labrador Brewing Company or Base Camp Brewing, both known for their bike-friendly atmosphere and excellent brews.
Route 3: Forest Park – An Urban Wilderness Escape (5-20 Miles, Moderate to Difficult)
For those craving a dose of nature without leaving the city, this ride is an absolute must. Forest Park is one of the country’s largest urban forests, a sprawling wilderness just minutes from downtown.  Â
The Route & Logistics
Distance: Variable, 5-20 miles
Terrain: Hilly approach with a rolling, car-free gravel path (Leif Erikson Drive)
Highlights: Leif Erikson Drive, “Witch’s Castle,” dense forest canopy.
Bald Hiker’s Highlights & Quirky History
Leif Erikson Drive: The main artery for cyclists is this beautiful, car-free gravel road that winds through the forest for over 11 miles. The dense canopy of firs and maples provides a cool, shaded escape even on a warm day.
The “Witch’s Castle”: A short detour off the main path will lead you to a moss-covered stone structure known as the Witch’s Castle. This eerie and photogenic ruin is actually the remains of an old park ranger station and has a surprisingly dramatic history, making it a popular and mysterious landmark.
A Cyclist’s Guide to Portland’s Best Coffee & Food Carts
Cycling and coffee are a perfect match, and Portland excels at both. Here are a few spots that are particularly welcoming to those on two wheels.
Bike-Friendly Cafes
Dragonfly Coffee House: A top spot among local cyclists, it features an outside window and seating, so you never have to lose sight of your bike. The owners are cyclists themselves and sponsor a local team.
Water Avenue Coffee: Located in the industrial inner southeast, this is a perfect place to start a ride, known for its expertly roasted coffee.
Cinco Siete: A gem in the Sellwood neighborhood where the owner offers cyclists a discount. It’s a great community hub with sunny outdoor seating.
Must-Try Food Carts
Portland’s food cart pods are legendary. After a long ride, nothing beats exploring the incredible variety of cuisines on offer.
Hawthorne Asylum: This massive pod on SE Hawthorne has a huge selection and a lively atmosphere with fire pits and covered seating.
Prost! Marketplace: Located on N Mississippi Ave, this pod is built around a German pub, allowing you to pair delicious street food with a cold pint of beer.
Frequently Asked Questions (FAQ)
After your bike ride you may want to go on an adventure in a book shop in Portland, not just any bookshop but Powell’s City of Books.
Looking at your photos this must have been a really fun trip. I have done the Seattle to Portland bike ride a couple of times and never spent enough time in Portland.
Hi Charlie, thanks yes I really enjoyed Portland.. I myself did not have enough time there. Must get back