10-18-2026 Pleasant Run and Pennsy Trails Ride
After a nice visit and lunch with family we decided to go on a bike ride and make the most of this cool but sunny day. We parked near the Fountain Square neighborhood and took the Cultural Trail south until we joined up with the Pleasant Run Trail. We followed that west into Irvington where we continued on the Pennsy Trail until the approaching sunset made us turn back. We returned to Fountain Square and enjoyed a Thai curry dinner at Siam Square, one of our favorite restaurants.
Ride facts
Date: Sunday, October 18, 2026
Route: Fountain Square → Indianapolis Cultural Trail → Pleasant Run Trail → Irvington → Pennsy Trail, returning to Fountain Square.
Distance: 22.4 miles (GPS track: 22.43 miles).
Time: 4:50 pm–7:31 pm EDT.
Trail notes: An out-and-back ride linking city trails, neighborhood streets and a former railroad corridor.
Highlights: Cool sunshine, the heron sculpture, Irvington’s Halloween decorations and fall color along the trail.
Food / after-ride stop: Thai coconut curry dinner at Siam Square in Fountain Square.
Trail background
Pleasant Run Trail
The Pleasant Run Trail follows Pleasant Run through Indianapolis, linking neighborhoods and green spaces. It provides a connection between Garfield Park and the Irvington area, making it a useful part of a longer city ride.
Pennsy Trail and railroad heritage
The Pennsy Trail takes its name from the Pennsylvania Railroad and follows part of its former rail corridor. What once carried trains now offers a paved route for walking and cycling, with the Indianapolis section passing through Irvington. The railroad heritage is a big part of what makes this more than just a path across town.
Trail background sources: https://www.traillink.com/trail/pleasant-run-trail/ and https://www.traillink.com/trail/pennsy-trail/
Photo log
We got to see the new apartment of our niece and her fiancé before going out for lunch with them and several other family members.
On the Pleasant Run Trail we both love this metalwork sculpture. It's a heron with a fish in its mouth.
A tree-lined bridge along the Pleasant Run Trail.
An interesting old bridge with low clearance - the sidewalk/bike trail dips down under the bridge for more clearance for pedestrians and cyclists.
There were lots more interesting Halloween house decorations since our last ride through Irvington.
Cara found this one particularly funny.
More Halloween decorations along our ride through Irvington.
Starting out on the Pennsy Trail in Irvington.
The Pennsy Trail passing through Irvington neighborhoods.
Further west the trail passes by several old, now defunct shopping malls.
Why do people like throwing their shoes up onto power lines?
Our break spot which was directly over an interstate.
We stopped beside a trail history marker and a bench.
A closer look at the trail history marker.
Fall color frames the trail as it crosses a small bridge.
The trail leads into a tunnel beneath the road.
Our dinner of a Thai coconut curry at Siam Square - this one had a spicy peanut sauce that's really good.
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