Trolley and Terwilliger Trails Loop

This loop offers a diverse cycling experience, transitioning from easy to moderate on the 40 Mile Loop Trail and Trolley Trail sections to moderate to difficult when you hit the Terwilliger Parkway. The Terwilliger portions involve significant inclines and winding roads, requiring good physical fitness. The total elevation gain is around 500 meters (1640 feet) over approximately 47.5 kilometers (29.5 miles).

You'll encounter mostly paved surfaces throughout the loop. The Trolley Trail sections are generally smooth, dedicated multi-use paths. However, be prepared for variable conditions on the Terwilliger Parkway, which can include bike lanes on roads and potentially some gravel or tree debris, especially after storms.

The estimated cycling duration for this 47.5-kilometer (29.5-mile) loop is around 2 hours and 24 minutes. However, this can vary significantly based on your fitness level, the number of stops you make, and how much you explore the various points of interest along the way.

Given the loop connects several communities, there are multiple parking options. You could look for parking near the Trolley Trail in areas like Milwaukie or Gladstone, or closer to the Terwilliger Parkway near Tryon Creek State Park or George Himes City Park. Public transport options are also available to various points along the route.

The loop offers a rich tapestry of sights. You'll ride along the historic Trolley Trail, pass by the Clackamas River, cross the Oregon City Bridge, and experience the iconic Tilikum Crossing. The Terwilliger Parkway also provides memorable views of the Willamette River and lush forested areas.

Yes, this route integrates well with Portland's extensive trail network. It utilizes sections of the Trolley Trail, Terwilliger Trail, and the 40 Mile Loop Trail. You'll also find connections to the Springwater Trail and the I-205 Multi-Use Path, which are part of Metro's regional trail system.

Generally, dogs are allowed on leash on most multi-use paths and trails in the Portland area, including sections of the Trolley Trail and Terwilliger Parkway. However, specific rules can vary by park or trail segment, so always check local signage. Ensure your dog is comfortable with cycling speeds and other trail users.

Spring and fall are often ideal for cycling this loop, offering pleasant temperatures and beautiful scenery. Summer can also be great, but be prepared for warmer weather, especially on exposed sections. Winter cycling is possible, but rain is common, and some sections of Terwilliger Parkway might have more debris or slick spots.

No, you do not typically need permits or pay entrance fees to cycle the Trolley and Terwilliger Trails Loop. These are public multi-use paths and parkways. However, if you plan to visit specific attractions or parks along the way, always check their individual policies.

Yes, as the loop passes through several communities like Milwaukie and Oregon City, you'll find various amenities. The Trolley Trail winds through vibrant business districts with cafes and eateries. Near the Terwilliger Parkway, you might find options closer to urban centers or along major roads. Accommodation is available in the broader Portland metropolitan area.

The suitability depends on the family's cycling experience. The Trolley Trail sections are predominantly flat, paved, and largely separated from traffic, making them very family-friendly. However, the Terwilliger Parkway introduces significant hills and winding roads, which can be challenging for younger children or less experienced family members. Consider doing only the Trolley Trail portion for a more relaxed family outing.