Hiking the Hidden Trails of Philadelphia's Great Woods

By Brian Schwarz

I was teaching at Temple University the year I wandered into the overgrown woods of West Fairmount Park with a very specific plan.

From satellite images, it looked like this entire section of the park might hold together as one continuous loop. Not a marked trail. Not something designed as it exists today. But something that hinted at an earlier structure. A system that may have once been part of a more elegant park layout, now grown over and left to evolve on its own.

I wanted to see if it still worked.

I started near Chamounix Drive with that loop already mapped out in my head. The goal wasn’t to wander. It was to stay within the shape of the woods and link together whatever paths remained to complete the full circuit.

Once inside, the overgrown nature of the woods was immediately clear. These weren’t manicured trails, and they weren’t marked. But they were there. Worn in just enough to follow, branching off in multiple directions, constantly giving you options.

And every so often, something would feel different.

A stretch that ran just a little too straight. A curve that seemed too deliberate. A sense that beneath the overgrowth, there had once been intention. Not obvious, not preserved, but still present if you were paying attention.

At each split, I made decisions based on orientation. I knew where the edges of the woods were supposed to be. I knew roughly how the loop should wrap. The question was whether the remnants of this older structure would still connect.

They did.

Moving through Belmont Woods, the terrain shifted in ways that confirmed where I was. Lower sections tightened with thicker growth and water moving through. Higher ground opened along the ridge near Chamounix. Even without signs, the landscape aligned with the plan.

At times, the presence of the Schuylkill Expressway defined the outer edge. Not something I needed to reach, but something that confirmed I was staying within the boundary of the loop.

The key point came at the crossing of Belmont Mansion and Chamounix Drive. That was the midpoint. If everything connected cleanly to that point, then the loop was real. I crossed once, exactly where expected, and went right back into the woods.

From there, it was about closing it.

The second half followed the same logic. Stay within the system. Keep the direction consistent. Use whatever path held the line of the loop, whether it felt like a worn trail or something that had simply been reclaimed by the woods.

And it held all the way through.

By the time I returned to where I started, I had completed just over five miles. One road crossing. No marked route. No need for one.

What looked like a possibility from above turned out to be fully walkable on the ground.

The overgrown woods of West Fairmount Park feel like something that was once shaped and then left behind. Not abandoned, but absorbed. If you understand how to read it, the structure is still there.

You don’t follow a trail here.

You follow what remains.

The Skyline Trail Is a Hike That Quietly Earns Its Ending

I started a hike at an ice rink and ended it on top of a mountain.

There was no dramatic beginning. Just a quiet start in Quincy, stepping onto the Skyline Trail with the intention of making it all the way to the end.

Early on, the trail gave me something unexpected. A still pool of water tucked between massive granite boulders. It felt hidden, like something you only notice if you’re really paying attention. 

And not long after, I realized something else. Even as the trail began to challenge you, there were always places to pause. Plenty of boulders to sit on, catch your breath, and take in the views.

The Blue Hills Reservation doesn’t hit you all at once. It unfolds. You go up and over one hill, then another, then another. Each one feels like a small destination. Each one gives you a slightly different perspective.

There were short sections where I had to use my hands and move carefully across the rocks. Not constant, just enough to keep you present. Just enough to remind you that you’re not just walking, you’re moving through the landscape.

What stood out most was that feeling of progression. It wasn’t about one big climb. It was about crossing something. Moving through it, not just up it.

And then, almost without realizing it, you arrive at Great Blue Hill.

You’re tired, but it’s the kind of tired that feels right. You look out, and it hits you. You didn’t just reach a high point. You got there step by step, starting from somewhere that didn’t feel like much at all.

That’s what stayed with me.

Not the summit.

The way you get there.

Hiking Mount San Jacinto from the Palm Springs Aerial Tramway

Mount San Jacinto offers one of the most unique hiking experiences in Southern California, and it starts in a way most hikes do not. Instead of climbing from the desert floor, you take the Palm Springs Aerial Tramway up to about 8,000 feet. In just minutes, you leave behind the heat of the Coachella Valley and step into a completely different environment of cool air, mountain silence, and towering lodgepole pines.

From there, the real hike begins.

The trail climbs another 3,000 feet through a landscape that feels almost unreal. Along one side of the mountain, an entire slope stretches out in massive white granite boulders. These are not small rocks scattered across the ground. They are enormous, some of them the size of buses, stacked and layered in a way that reshapes the entire mountainside.

Rising above and between them are tall lodgepole pines, straight and steady, creating a striking contrast between living forest and solid stone.

As you get closer to the summit, the environment changes again. The trees disappear, and you move into a wide, open mountainside covered in low shrubs. The shrubs are filled with small flowers, and bees move constantly between them, creating a quiet hum in the air. They are everywhere, but they do not bother you. You simply walk through the space, surrounded by movement and sound.

Then the final stretch begins.

You are no longer just hiking. You are climbing. The trail leads you onto the same massive white boulders you saw from below. To reach the top, you have to scramble, using your hands as well as your feet, moving carefully across the rock. It feels raw and physical, like the mountain is asking a little more from you before it gives anything back.

At the very top, you climb up and around the highest boulder, and that is when it opens up.

The view is beyond anything you expect. One direction stretches across the Inland Empire, past Los Angeles and Santa Monica, all the way to the Pacific Ocean. Another drops into the vast Coachella Valley. To the north, layers of mountains rise and fade into the distance.

It is the kind of reward you do not forget.

Mount San Jacinto is not just a hike. It is an experience you earn.