Pennsy Trail

About the Pennsy Trail

The Pennsy Trail turns a historic transportation corridor into a smooth way to experience Indy’s east side and the countryside beyond, reusing the former Pennsylvania Railroad right-of-way and running close to U.S. 40, the Historic National Road. It’s part of the bigger National Road Heritage Trail vision, a developing, cross-state route that aims to connect communities by linking together multiple built segments over time.

In Indianapolis, the Pennsy begins in the heart of historic Irvington, a 1920s-era streetscar suburb where the vibe is neighborhood-forward and easy to pair with a park break or a casual out-and-back ride. From there, the trail heads east and the experience quickly shifts into that classic rail-trail feeling of steady lines and a gentle grade. One of the signature moments is the restored railroad trestle over Shadeland Avenue, a dramatic “wow” crossing that lifts you above busy traffic before dropping you back into quieter miles.

Continuing toward Cumberland, the Pennsy delivers a fun mix of textures: wooded corridors and a few industrial edges that underscore the rail history. You’ll find interpretative signage about the history along the way, as well as a fun section in Cumberland with scaled-distance signs of the solar system planets.

Beyond, you’ll find open views as you roll into farmland. Riders also pass multiple restored railroad bridges, which gives the route that satisfying sense of moving through a living piece of infrastructure history rather than just a simple path from point A to point B.

Farther east, the Pennsy reappears as a strong, well-loved segment in Greenfield, where the trail leans even more into a calm, “get-in-the-miles” rhythm through greener edges and small-town scenery. A highlight here is the crossing over Brandywine Creek, which local trail descriptions often connect to James Whitcomb Riley’s enduring imagery of Indiana waterways and countryside.

Right now, the Pennsy is best enjoyed as two main rideable areas (Indy/Cumberland and Greenfield), with a remaining gap between them that local partners are actively working to close as the corridor grows toward a more continuous National Road Heritage Trail route.