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The straight, paved Pennsy Trail (not to be confused with the Pennsy Greenway located farther north in the Chicago suburbs) occupies a portion of the old right-of-way of the Pennsylvania Railroad (“Pennsy” for short) and parallels the historic Old National Road. The Indiana portion of the corridor extended from Richmond, Indiana, through Indianapolis to the eastern border of Illinois. Along these tracks, the body of President Abraham Lincoln was carried back to Illinois on April 30, 1865.
The trail is currently open in two main, disjointed segments. The western segment begins on the eastern side of Indianapolis, linking the Irvington neighborhood with a local elementary school and a large Indiana Department of Transportation complex. The trail route follows the side of Ritter Avenue to create a connection with Ellenberger Park and the Pleasant Run Trail; heading east on the rail corridor, a restored railroad trestle takes trail users over busy Shadeland Avenue.
Local trail managers completed a crucial link on the trail in 2021, allowing for a seamless journey between Indianapolis and neighboring Cumberland. This section passes industrial properties and crosses several restored railroad bridges through a wooded corridor before emerging into open farmland. The trail parallels US 40 for its entire length (although the highway is always out of view) and thus offers a much safer biking and walking alternative. The trail comes to a halt at a trailhead at County Road 600 W, which offers a small but convenient parking area.
Further east, the Pennsy Trail resumes in the city of Greenfield after a gap of about four miles - a mile-long section of trail was built between County Road 500 W and County Road 400 W in 2021, but this portion is not easily accessible from the main trail until future extensions are completed. Passing through farmland and the Greenfield Country Club golf course, the trail also traverses neighborhoods and is within a short walking distance of downtown. The nearly 6-mile stretch of trail crosses Brandywine Creek, alleged to be the creek where the "Old Swimmin' Hole" was found in James Whitcomb Riley's poem of the same name.
Plans call for all three open segments to be linked into a single Pennsy Trail in the future. The trail is also set to become one of the vital components of the National Road Heritage Trail, a proposed border-to-border trail stretching more than 150 miles between Terre Haute and Richmond, Indiana, on the abandoned Pennsylvania Railroad corridor.
In Indianapolis, parking is available at Irvington Plaza, midway along the trail (6243 Washington Street; park near the Dairy Queen just south of the Marsh grocery store).
In Cumberland, park at either of the two large shopping centers on both sides of S. German Church Road off E. Washington Street/US 40. Direct connections to the trail can be found in the parking lots. Additional parking is available at the trailhead at County Road 600 W, just off US-40.
In Greenfield, parking is available at each end of the trail: at CR 150 W and at CR 400 E, which also offers a portable toilet. Closer to downtown, you can park at Center Street and at Morristown Pike.
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