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Routes
Bike touring routes & trails
United States
Oregon
Clackamas County
Milwaukie

Trolley Trail Loop

Moderate

3.3

(23)

88

riders

Trolley Trail Loop

01:30

31.3km

180m

Cycling

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 an elevation gain of 576 feet (176 metres), which typically takes about 1 hour and 29 minutes to complete. As you…

Last updated: April 23, 2026

Waypoints

A

Start point

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1

160 m

Willamette River

Highlight • River

The Willamette River, a vital force in the Northwestern United States, weaves through the region, contributing significantly to its intricate drainage system as a major tributary of the Columbia River.

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2

9.96 km

Clackamas River

Highlight • 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 …

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B

31.3 km

End point

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Way Types & Surfaces

Way Types

31.1 km

157 m

< 100 m

< 100 m

Surfaces

18.0 km

12.8 km

484 m

< 100 m

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Elevation

Elevation

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Highest point (80 m)

Lowest point (10 m)

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Weather

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Today

Thursday 7 May

21°C

11°C

0 %

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Max wind speed: 10.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the overall difficulty of cycling this route?

This loop is considered an "easy" ride, making it suitable for families, beginners, and those looking for a relaxed touring experience. It features mostly flat terrain with minimal climbing, encouraging a leisurely pace.

What kind of terrain will I encounter on the trail?

The route is predominantly a paved, multi-use path, ideal for touring cyclists. It includes sections of the Trolley Trail, Springwater Corridor, and the I-205 Multi-Use Path. While primarily paved, some segments may transition between concrete and asphalt. You'll also navigate some urban areas with road crossings, many of which have signalized crossings.

What are the best times of year to cycle this loop?

The trail is enjoyable year-round, but spring and fall offer the most pleasant cycling conditions with mild temperatures and beautiful scenery. Summer can be warm, so plan for early morning or late afternoon rides. Winter cycling is possible, but be prepared for rain and cooler temperatures.

Are dogs allowed on the Trolley Trail Loop?

Yes, dogs are generally allowed on the multi-use paths that make up this loop. Please ensure your dog is kept on a leash and that you clean up after them to maintain a pleasant experience for all users.

Do I need any permits or pay entrance fees to use the trail?

No, there are no permits or entrance fees required to access and cycle the Trolley Trail Loop. It is a publicly accessible multi-use path system.

Where can I park to access the Trolley Trail Loop?

Parking is available at various points along the loop, particularly near parks like Cross Park, Riverfront, Milwaukie Bay Park, and Stringfield Family Park. Many urban sections also offer street parking or dedicated parking lots for trail users.

What amenities are available along the route?

You'll find various amenities along the way, including restrooms, picnic areas, and even a bike repair station in Oak Grove for on-the-go maintenance. The route also passes through charming small cities where you can find cafes and other services.

What scenic highlights can I expect to see?

The loop offers diverse scenery, including charming urban areas, residential neighborhoods, and several parks. Key natural highlights include scenic views along the Willamette River and the Clackamas River. You might also spot wildlife in natural areas like the Tideman Johnson Natural Area and enjoy unique art installations by local artisans.

Does the trail connect to other cycling routes or public transport?

Yes, this loop is an integral part of Portland's larger 40-mile regional trail system. It offers convenient connections to the MAX Orange Line, allowing you to combine your ride with public transit by utilizing the designated bike rack spaces on MAX trains. The route also passes through sections of the Veteran's Memorial Greenway, I-205 Multi-Use Path, Trolley Trail, and Springwater Trail.

Is the Trolley Trail Loop suitable for families with children?

Absolutely! With its mostly flat, paved, and car-free sections, this loop is an excellent choice for families and less experienced cyclists. The gentle terrain and varied scenery make it an enjoyable and safe outing for all ages.

What makes this trail historically significant?

The route traces the path of the historic Portland Traction Company interurban trolley line, which operated from 1893 to 1968. Cycling this trail offers a unique connection to the region's past, blending history with outdoor recreation.

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11:16h

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