This loop starts and ends on the parking by Bear Mountain. You hike thought the woods, up and down hills, over stony terrain, on narrow trails. There are a few shortcuts to get back to the parking area in case you don't want to do the entire loop. Both the distance and terrain make this a challenging loop. To finish the entire loop may take between 12-14 hours if you're hiking it, so the proper amount of fluid and food is necessary.
In case you won't be able to make the loop, the best shortcut to get back to the parking lot is from the Appalachian Trail after you've gone 11.5 miles. From there, it is 15min hike path going to the parking lot.
Start from parking, which is located at Anthony Wayne Dr, Tomkins Cove, NY 10986 (GPS; 41.291421, - 74.024834). There are two parking lots at Anthony Wane Recreation Area.
You start the trail on the Anthony Wayne Trail
(marked with a white rhombus and signs for "Bike Trail"). This way you go towards the woods. Then you turn left uphill and follow the Fawn Trail
(marked with a white rectangle and the red letter F). Then you make a left to trail marked with a blue rectangle (Timp-Torne Trail
). That way you're going on summit of the hills.
Next you follow a trail marked with a white circle with the blue sign 1777W (1777 West Trail
). You have to cross the Route 6, turn right toward Queensborough Road. Follow the route and you'll pass buildings on the left. Then you turn right and you pass the pistol range. Follow the 1777 West Trail
. After you pass the pistol range, follow a trail marked with a white circle and a sign for 1779. You'll pass a lake on the left. Then you follow the white rectangles with red squares (Popolopen Gorge Trail
). You're going up hill.
Next you follow a path marked with a green rectangle, the Long Path: Section 6
. You're going through the woods, past a parking lot, across Long Mountain Parkway, and following the trail in the woods.
Keep following Long Path: Section 6
—you'll go up hill, and pass a shelter on the summit of the mountain. Follow the route in the woods.
Make a right and follow markers with a yellow rectangle (Menomine Trail
). You pass the lake on the right and later you reach a parking and place with picnic tables. Take a break, eat something, and drink‚—you'll need to refuel as it's still long way to go.
Continue on Menomine Trail
, still following yellow rectangles. You'll pass two small buildings by the lake and follow the path in the woods. You go uphill and pass another shelter. After you pass the shelter, follow the AT: New York-New Jersey Section
, marked with white rectangles, by turning left. You follow the trail uphill, through woods. On the right, you should have a view of Manhattan while following the trail.
You go downhill, towards Palisade Parkway. You pass Palisade Parkway twice and go to the woods and follow Appalachian Trail. Later, the route is uphill. Later, you turn right and follow blue rectangles (Timp-Torne Trail
). You going uphill and will see fork. On the right side, you'll see a shelter. You follow the yellow rectangles at this time (Suffern-Bear Mountain Trail
). You'll pass a settlement called Doodletown. Following the trail through the woods, you'll pass Seven Lakes Drive. Then, you go all the way to get to the bottom of the Bear Mountain. You'll see a lake on the right side.
Then you go back to the Appalachian Trail, marked with white rectangles, up hill to the Bear Mountain summit. On the summit, you'll see the Hudson River. Then you follow the Appalachian Trail, and you go downhill, following the path in the woods.
Then you leave Appalachian Trail by turning left and following a white marking with a letter F (Fawn Trail
). And, at last, you follow the Anthony Wayne Trail South
(white rhombus with "Bike Trail") back down to the parking lot.