On Sunday, April 6, 2025, after having lunch on the Riverwalk with family, we headed out to the south side of San Antonio to ride the Pleasanton Road Trail which is part of the larger Howard E. Peak Greenway Trails System of San Antonio and the surrounding area.

The Pleasanton Road Trail winds it’s way northward until it eventually joins up with the Riverwalk Trail that takes you into downtown (part of the Medina River Greenway).

This trail system has to be one of the best maintained and interesting in all of the ones we have ever ridden. You would not even imagine the beauty that is out here while driving to the trailhead parking. The drive to the trailhead parking lot is in the middle of nowhere (see data link below for exact location and ride map). It looked very sketch and desert like as we approached the lot.

However, we were pleasantly surprised by the instant change in scenery once we turned in to the lot to park. There were mesquite trees all around, water stations, and the trail maps were fantastic!

The entire trail looked like these photos. There were trees everywhere, prickly pear cactus in bloom all along the wide completely paved trail. Restrooms, water stations, and resting areas were located all along the route, as well. The trail follows the San Antonio River for a while and it is beautiful.

Purple Martins

We came upon some folks fishing here and there, but the most amazing part of the trail to me was the mile or two that we rode through the Purple Martins and Dragonflies, which you can see below. Essentially, the purple martins grab the dragonflies out of mid-air to eat and because this particular stretch was overloaded with dragonflies, both were zooming all around us.

It was similar to being in an area where there are a lot of hummingbirds. You are seriously concerned that they are going to run right into you, but the never do. After a few minutes of riding through the fray, we noticed that it became almost like a nature dance of some sort. It was so amazingly beautiful to behold. An experience I am not soon to forget.

Rest Stop on the Trail

So Many Bridges

Many bridges dotted the path, as well, keeping the ride constantly interesting. We enjoyed this ride so very much and were so glad we took along our bikes on the trip. If you get a chance to ride this one, take it. It is well worth the trip.

Ride with GPS Route

Below is the embed for our actual Ride with GPS profile ride from this trip, you can click on the title for more details.