Distance: 2.7 miles
Skill Level: moderate to difficult
Elevation Gain: 500′
Type of Hike: out-and-back
Trail Condition: field, road, rocky
Wow Factor: views, wild cactus
Note: poles recommended, especially if you’re front carrying
How to get there: The parking lot is located off 9D (5 miles south of 301, 4 north of the Bear Mountain Bridge). You will see a little brown sign saying Castle Rock Unique Area hanging from a post and two stone pillars on either side of the gravel Wing and Wing Road. The drive is almost parallel with the Garrison “Let’s Go Take a Hike” sign and the golf course. Follow signs for the small parking lot.
Address to get you close: 854 Wing and Wing, Garrison, NY 10524
Summary: From the parking area, head back down the road the way you came. Turn left on the road heading up toward the castle gate. Bear right with the road and look for red markers.
Make a left into the field and follow the mowed path and start your climb. Its gradual but unrelenting. Turn around to rest your calves and check out the view of West Point. The trail will split and you can go either. If you go straight, you will enter the treeline and see a gazebo that looks like it belongs in Game of Thrones.
Turn right on the woods road. Keep on red at the intersection with blue. This is the steeper part of the road trail. Keep following red up the hill back and forth, back and forth.
At the next intersection with blue, turn right onto the steep red trail. Going up this trail is hard but I had to butt-slide down with a baby on my front. This trail walks along the top of the ridge. The views would probably be better when the leaves are down but pretty anyway. This part does seem to go forever. You see open space ahead and think its the end but its not.
Eventually, you will reach the end with views of Bear Mountain Bridge. Look around for the wild growing cactus. Yes, cactus on a mountaintop in lower New York! This is a great area for littles to explore and rock climb, just be careful of steep sections. Have a snack and rest your weary legs, then head back down being very careful.
Dogs: on a leash no longer than 10 feet
Map, in Best Hikes with Dogs NYC and Beyond but its the better