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Routes
Cycling routes
United States
Oregon
Clackamas County

Milwaukie

The best cycling routes around Milwaukie

4.6

(308)

3,646

riders

247

rides

Touring cycling around Milwaukie, Oregon, is characterized by its location along the Willamette River, offering scenic waterfront routes. The region features a network of well-maintained trails that traverse wetlands, urban parks, and former railway lines. Gentle elevations are common, with routes often following river courses and connecting to broader regional trail systems. The landscape provides a mix of natural beauty and accessible urban cycling opportunities.

Best touring cycling routes around Milwaukie

  • The most popular touring cycling route is Trolley Trailโ€ฆ

Last updated: April 25, 2026

4.6

(8)

25

riders

#1.

Trolley Trail Loop

31.3km

01:30

180m

180m

The Trolley Trail Loop offers a moderate touring cycling experience through a diverse landscape, blending urban charm with serene natural passages. You will cover 19.5 miles (31.3 km) with anโ€ฆ

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Moderate

Embark on a moderate touring bicycle adventure along the Boring Loop, a 43.3-mile (69.7 km) route that promises diverse scenery and a rewarding ride. You will gain 1379 feet (420โ€ฆ

Moderate
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Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Hard bike ride. Very good fitness required. You may need to push your bike for some segments of this route.

Hard

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Tips from the Community

mtm05005
May 23, 2025, Clackamette Cove

Clackamette Cove is a small lake off of Clackamas River. The Clackamas River Trail runs right along the banks of the lake. It is definitely worth taking a break somewhere along the lake to enjoy the views.

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Andrus
May 15, 2025, Boring, Oregon

Boring, Oregon has become somewhat famous, or infamous, depending on how you look at it. In recent years it has become well known due to its humorous take on its name and partnering with Dull, Scotland as "sister cities" in order to promote tourism to both locations.

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Elizabeth
January 13, 2025, Willamette River

Nice path so you donโ€™t have to run with cars.

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The Broadway Bridge was built in 1913. It was originally black, but was repainted red in 1963.

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Alex
September 23, 2024, Willamette Greenway Trail

The Willamette River stretches over 255 miles from Cottage Grove in the southern Willamette Valley to Portland, where it meets the Columbia River. The Multnomah Channel branches off near Sauvie Island before joining the Columbia. The Willamette River Greenway offers a few open green spaces along the riverbanks, some with boat launches and basic amenities. Bikers also pass through preserved areas for native wildlife and with scenic views. This trail is a popular destination for biking, walking, and running along its shared paths.

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Alex
September 19, 2024, Tilikum Crossing

Tilikum Crossing, Bridge of the People, is a cable-stayed bridge designed by TriMet for MAX Orange Line trains, buses, streetcars, cyclists, pedestrians, and emergency vehicles. Opened on September 12, 2015, it prohibits private cars and trucks, making it the first major U.S. bridge built for transit and non-motorized traffic only. Named after the Chinook word for "people," it was the first new bridge over the Willamette River in Portland since the Fremont Bridge in 1973. Construction began in 2011.

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Andrus
September 13, 2024, Clackamas River

The Clackamas River gets its name from the Clackamas people who have lived in the area for hundreds of generations. Though much of the river's course has been developed 47 of its 83 miles are designated as NWSRS (National Wild and Scenic River System)

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Andrus
September 11, 2024, Eastbank Esplanade

The Eastbank Esplanade was brought about by the 1996 Willamette Valley Flood. After that flood washed out the existing !-5 bike bypass and new path was needed and the Eastbank Esplanade was born.

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Frequently Asked Questions

How many touring cycling routes are available in Milwaukie?

Milwaukie offers a diverse selection of 13 touring cycling routes, catering to various skill levels. You'll find 4 easy routes, 8 moderate routes, and 1 more challenging option to explore the region's scenic landscapes.

What is the best time of year for touring cycling in Milwaukie?

The spring and fall months generally offer the most pleasant conditions for touring cycling in Milwaukie, with mild temperatures and less rain. Summer can also be excellent, though it's wise to start earlier in the day to avoid the midday heat. While some trails are accessible year-round, winter can bring cooler, wetter weather, so appropriate gear is recommended.

What are the typical terrain and elevation like on Milwaukie's touring cycling routes?

Milwaukie's touring cycling routes are largely characterized by gentle elevations, often following river courses like the Willamette River. Many routes utilize well-maintained, paved trails that traverse wetlands, urban parks, and former railway lines. While some routes, such as the Boring Loop via Springwater Corridor and Trolley Trail, include gentle climbs, the overall terrain is generally accessible for touring cyclists.

Are there any family-friendly touring cycling routes in Milwaukie?

Yes, Milwaukie offers several family-friendly options. Routes like the Eastbank Esplanade โ€“ Springwater Corridor loop from Milwaukie/Main Street are rated as easy and feature mostly car-free, paved sections, making them suitable for families. The region's commitment to active transportation means many trails are designed for comfortable, safe cycling.

Which touring cycling routes are circular or loop trails?

Several popular touring cycling routes in Milwaukie are designed as loops, offering varied scenery without retracing your steps. Notable examples include the Trolley Trail Loop, the longer Boring Loop via Springwater Corridor and Trolley Trail, and the Eastbank Esplanade โ€“ Springwater Corridor loop from Milwaukie/Main Street.

What scenic viewpoints or natural attractions can I expect to see along the routes?

Milwaukie's routes offer numerous scenic highlights. You'll enjoy picturesque views of the Willamette River, especially along trails like the Trolley Trail Loop. The region is also home to natural areas such as Oaks Bottom Wildlife Refuge, known for its diverse wildlife, and Elk Rock Island, accessible during low water. You might also pass by the Clackamas River or enjoy views from places like Mount Tabor or Viewpoint in Powell Butte Nature Park on some extended routes.

Are there any long-distance touring cycling routes in the Milwaukie area?

For those seeking longer rides, Milwaukie serves as an excellent starting point. The Boring Loop via Springwater Corridor and Trolley Trail is a substantial 43.3-mile (69.7 km) route that combines two major regional trails. Another great option is the Springwater Corridor โ€“ Willamette River loop from Southeast Park Avenue, which covers approximately 45.9 miles (73.9 km).

What do other touring cyclists enjoy most about cycling in Milwaukie?

The touring cycling routes in Milwaukie are highly regarded by the komoot community, boasting an average rating of 4.5 stars from over 250 reviews. Cyclists frequently praise the region's well-maintained, mostly paved trails, the beautiful riverfront views, and the accessibility of routes that connect urban areas with natural landscapes. The variety of options, from easy loops to longer journeys, is also a common highlight.

Is public transport accessible near Milwaukie's cycling routes?

Yes, public transport is well-integrated with Milwaukie's cycling infrastructure. The Springwater Corridor, a key part of many touring routes, has connections to public transport, making it convenient to access various sections of the trail system without needing a car. This allows for flexible planning of your cycling adventures.

Are there places to park near the touring cycling routes in Milwaukie?

Yes, parking is generally available near popular access points for Milwaukie's cycling routes. Areas like Milwaukie Riverfront Park and Milwaukie Bay Park offer convenient parking options, providing easy access to the Willamette River trails and connections to the broader network. It's always a good idea to check specific starting points for detailed parking information.

Are there any specific permits required for cycling on Milwaukie's trails?

Generally, no specific permits are required for recreational touring cycling on the public trails and paths in and around Milwaukie, such as the Trolley Trail or Springwater Corridor. These trails are part of the public park and transportation network. However, always be mindful of local regulations and signage, especially in protected natural areas.

Can I find cafes, pubs, or accommodation along the touring cycling routes?

Milwaukie's routes, especially those passing through urban areas or connecting to larger trail systems like the Springwater Corridor and Trolley Trail, offer access to various amenities. You'll find cafes, pubs, and dining options in Milwaukie and neighboring communities. For accommodation, there are options available within Milwaukie and the wider Portland metropolitan area, providing convenient stays for touring cyclists.

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