This route follows a ridge with great views to both the east and west along the way. It's best in the fall and winter as hikers will be treated to more unobstructed views.
The hike starts at a small park in Woodbury called Gonzaga Park. The park itself is closed from mid-November to April, but you'll still be able to park just outside the gate to access the trails. There are three different trail names that share this path. The Jessup Trail
starts/end at Gonzaga Park and travels through all of Schunemunk State Park. The Highlands Trail and the Long Path also share this trail, so along the way you'll see these markers for these three individual trails.
The trail follows the Schunemunk Ridge the entire way on an easement trail through private property. The ridge can be narrow in places, and in winter you'll enjoy open views to the east and west. Once you get to the top of the ridge, there is not much more elevation gain.
This section ends when you reach the trail junction with the Western Ridge Trail
in Schunemunk State Park. The Long Path also breaks off here, descending off the ridge to the east. This is a good place to turn back but if you have time you can hike a three-mile loop of the Western Ridge Trail
- Ridge-to-Ridge Trail
and back on the Jessup/Highlands Trail.
If you add that loop, the total distance is 10.8 miles with an additional 700 feet of elevation gain. I did this hike in early December and had the entire hike to myself.