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The Major Taylor Trail is named after legendary African American cyclist Marshall “Major” Taylor, who was one of the most celebrated bicycle racers of the late nineteenth century, setting several world records and winning numerous races all over the world. One of Chicago's few truly urban trails, the Major Taylor Trail connects several neighborhoods on the city's southwest side.
The trail starts and ends in areas managed by the Forest Preserves of Cook County: Dan Ryan Woods in the north and Whistler Woods in the south. The northernmost section of the trail—from Dan Ryan Woods to 87th Street—is on an elevated portion of the former train line. Its only street crossing (at 83rd Street) is an overpass with the street below.
The rest of the trail and street crossings are at ground level. The busier street crossings are all assisted with traffic lights or stop signs. At the 95th Street crossing, there's a cluster of fast food restaurants, making this a popular rest stop along the trail. From 95th to 105th Streets, the trail is on city streets, passing through a very nice, tranquil neighborhood.
The rail-trail portions of the trail show ample evidence of their purposed past: tree-lined corridors, nearby industries, and wide right-of-ways. The trail crosses I-57 on an old railroad bridge, and it crosses the Little Calumet River on a cantilevered trailway beside a railroad bridge still in use.
Along its route, the trail has many connections with other modes of public transportation. There are CTA bus stops at or near the busier street crossings, and there are METRA train stations at or near two of the railroad crossings. The southern end of the trail will someday connect with the Cal-Sag Trail, which is now approaching from the west.
Parking is available on either end of the trail: on the north side at Dan Ryan Woods (S. Western Ave. and W. 87th St., Chicago) and on the south side at Whistler Woods Forest Preserve (off Forest View Ave., east of S. Halsted St., in Riverdale).
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