Also part of Glenclyffe Loop, Arden Point, Marcia’s Mile
Distance: 2.5 miles, option for more
Skill Level: easy
Elevation Gain: 200′
Type of Hike: double loop
Trail Condition: road, grass, trail, rocky
Wow Factor: views of Hudson and monastery (friary), historic value
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
You can also do this hike from the Garrison Train Station, just follow blue south.
Summary: From the parking lot, head back down to 9D. If you look back over your shoulder, you’ll see the castle up on the hill. Carefully cross the road, climb the short wall and head south/left on the grass (yes, really!). Pass the take a hike sign and head catty-corner into the woods, looking for red and white blazes. You’ll follow the pond and see where it spills out on the dam. Find the kiosk for more historical information about Benedict Arnold’s flight along this hike. You’ll pass through a cool bamboo pocket. A fun place to explore with little ones. The trail can be a little narrow or completely disappear on this section so keep your eyes peeled for the blazes.
Head down hill until the trail splits. Hang a left for a seasonal viewing platform where Arnold boarded a boat and escaped. Backtrack and head north/right/straight to keep going. You will dump out on a road. Follows signs left, then left again back into the woods. Keep heading north and you will start to see some nice views of the Hudson and will cross in front of the Monastery (actually a friary that is not part of the town recreation department). There is a nice bench out front and if you search, you will see a little waterfall on the other side of the river.
Head down the hill and around overgrown bushes and pick up the trail again. Keep going north until you get to the gazebo–a great place to play. Jump back on the trail, heading north/left.
Arden’s Point, extra mile option: At the intersection, go straight/left/north following orange on the road. At the intersection with blue, turn left and head over the train tracks on the bridge. The Arden Point Loop follows red along the river, with a few areas to go down to the waters edge and take in the view of West Point, and blue, closer to the train tracks and not as well maintained. You can go either way then meet back at the bridge and head south on orange. (You could go check out the train station if you want by following blue north.)
At the intersection with the gazebo, turn right/east (left if you did Arden’s Point) following white markers to head back to the car. Follow the road up, cut across the grass, down the wall, and cross 9D to Wing and Wing and up to your car.
Map, or a photo of one