Skip the crowds at Cobble Lookout for solitude on Winch Mountain

Hidden bushwhack offers better views without the hordes of hikers

By Tim Rowland

The Cobble Lookout Trail in Wilmington is scarcely a decade old, but it did not stay a secret for long. Just a mile and change one way, a scant 280-foot elevation gain and a fantastic panorama of the West Branch of the Ausable River Valley conspired to make a hiker magnet of this little slice of the park.

Well, nuts to that.

For just a little extra investment in time and energy you can have your own personal Cobble Lookout with better views and without the crowds. Or all that loose cobble from which Cobble Lookout takes its name, for that matter.

Just a mile past the Cobble overlook is Winch Mountain, a nondescript hump in the Stephenson Range that, on its southeastern flank, just happens to have a broad slab of smooth, open rock maybe 50 yards wide that looks down almost directly ont the Santa’s Workshop theme park on the Whiteface Veterans Memorial Highway.

The only downside is that it’s just around the bend from Cobble Lookout itself, so you can’t look down with bland condescension on the dozens of hikers elbowing each other thereon. Nor can they see you, more’s the pity, smugly stretching out on a mountain to call your own.

The bushwhack to Winch Mountain

Of course being a bushwhack it takes a little extra starch in your britches to access the Winch overlook, but there’s nothing terribly tricky about it.

Actually that’s not completely true. These expansive rock outcroppings that look so obvious from the valley can be devilishly hard to find when you’re in the middle of a leafy, zillion-acre forest.

The first mile-plus of the hike is no problem, because you’re simply following the Cobble Lookout trail, whose trailhead is 3.3 miles from the four-way stop in Wilmington. Take Rt. 431 for 3 miles and bear right on Gillespie Drive, with the trailhead and its mockingly small three-car parking lot on the right.

The Cobble Lookout trail quickly passes a rock cliff climbing wall on the left, then knocks along the contour for another mile never gaining or losing too much in the way of elevation. The trail has taken a beating though from so many boots, and is eroded and muddy in spots.

Just before reaching the overlook, a rather obvious old woods road is apparent on the left. You can follow this, after a fashion, to the northeast for about a third of a mile, at which point the main obstacle between you and the bald nose of Winch is a not-inconsiderable ravine through which babbles Stephenson Brook.

I reckoned we could avoid this deep cleft by paralleling the brook from high on the hogback until the stream rose to meet us, at which point we would double back on the far side of the gulch. We couldn’t double back too far though, or we would come out at the bottom of the cliff instead of the top. Which, naturally, is exactly what happened.

In the end, you can pick your poison. You can aim for the top of the cliff, but that will land you in some heavy spruce. Aiming for the bottom keeps you in open hardwood, but then you have to scramble up the steep approach to the rock—which in truth is kind of fun.

So how do you know exactly where this cliff is located if you are in the midst of heavy, low-visibility forest? You cheat, that’s how. I used the satellite imagery from onX Maps, upon which the cliff was quite apparent.

Purists might shudder in horror, and 20 years ago I might have agreed, but at my age I believe I have earned the right to play from the “senior tees,” so to speak.

Views surpass popular Cobble Lookout

And there can be no arguing with the views, which are similar to Cobble Lookout but more dramatic. You can see the theme park, the cuts of the Whiteface Highway as it approaches the summit, the Green mountains of Vermont and the hamlet of Wilmington and its horrid new RV park that can likely be seen from space.

On the way back, we avoided the lengthy switchback and simply skidded down to the bottom of the ravine and climbed back out—which wasn’t as bad as the topo map made it out to be.

All told, we logged 4.5 miles and gained a rather tame 700 feet in elevation. It should also be mentioned that along the way we encountered multiple old logging roads, hunters paths and paths of actual herds of the four-footed variety. And few if any of them are going where you want to go, at least not for the long haul.

But if you’re comfortable off-trail and want a big slab of bare rock to call your own, Winch can be had with, as bushwhacks go, a rather minimal amount of effort.