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The Trolley Trail follows the Portland Traction Company's Oregon City Line streetcar right-of-way, serving Portland’s metro area, that ran between Milwaukie and Gladstone from 1893 until 1968.
Currently, 6 miles of the trail are complete. The trail is part of a planned 20-mile loop that will connect Portland, Milwaukie, Gladstone, Oregon City, and Gresham—linking schools, parks, commercial districts, and historical sites along the way. Metro and the North Clackamas Parks & Recreation District (NCPRD) purchased the right-of-way in December 2001. Developed in 2012, the trail completes a missing link in Metro's regional trail system. It presently reaches bike lanes in Milwaukie and Gladstone and will eventually link to both the Springwater Corridor and the I-205 Multi-Use Path.
Milwaukie Riverfront Park on the Willamette River provides a great starting point. Summer Sundays bring the farmers' market just across the street. As you make your way along the trail, wide corridors of trees and grass buffer you from city streets; you may encounter a host of wildlife, including opossums, beavers, great blue herons, green herons, and Western screech-owls.
On either side of the length of the trail, you'll find historic homes claiming many styles of architecture, including Arts & Crafts, Craftsman, Queen Anne, Colonial Revival, and more. Just past Courtney Road to your left, the Elizabeth Heitkamper House, completed in 1888, is the largest and most prominent example of Queen Anne–Vernacular style in north Clackamas County.
The trail passes through the playgrounds and nature areas of Stringfield Park, eventually ending at East Jersey Street in Gladstone. After this point, you'll find intermittent bike lanes and sidewalks.
In the next couple of years, the trail will extend 1 mile north along SE 17th Avenue to reach the Springwater Corridor. Currently, this section of street riding is used by seasoned commuters and is not recommended for families or trail riders.
To reach Milwaukie Riverfront Park from downtown Portland, take State Route 99E (which later becomes SE McLoughlin Boulevard) about 6 miles south to SE Jefferson Street. You'll find a large, paved lot situated by the river on your right.
To reach the Stringfield Park trailhead (mid-trail, 3614 SE Naef Road), from downtown Portland, take SR 99E (which later becomes SE McLoughlin Boulevard) about 9 miles south, and turn left onto SE Naef Road. Stringfield Park will be on your left.
Street parking is available at the trail's southern endpoint at E. Jersey Street and Portland Avenue in Gladstone. Take Interstate 205 to Exit 11, and head west on 82nd Drive for 0.3 mile. Turn right onto E. Arlington Street, and go 0.5 mile. Turn right onto Portland Avenue, and in 0.4 mile, you will arrive at the trailhead.
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