Hang Glider Overlook and High Point Overlook via the Long Path
Directions to trailhead
NY State Thruway I-87 North to exit 21B. Turn right on US-9W North towards Ravena. Continue on US-9W North for 6.9 miles then turn left on CR-101. In 3.6 miles turn left on Bridge Street. Proceed another 6.4 miles then turn right on Tarrytown Road. In 1.4 miles turn left on Delaware Turnpike then in 1.9 miles turn right on Highway 85. In 2.2 miles turn left on NY-157/Thacher Park Road. In 4.4 miles turn right on Ryan Road and follow .4 mile to parking at the end of the road.
Although the park charges a seasonal parking fee, parking at the end of Ryan Road is free.
Facing the kiosk and map box, the yellow-blazed Perimeter Trail to the immediate left will be the return route. Turn right and look for the continuation of the yellow trail, which enters the woods on a footpath at the park sign.
In one tenth of a mile keep straight when a woods road crosses over and cross a wooden footbridge in another tenth of a mile. The yellow trail ends .35 mile into the hike at an intersection with the aqua-blazed Long Path. Turn left on the Long Path.
In .7 mile white connector trail W1 goes straight. Connector trails are identified by a number preceded by “W”, marked at intersections. At this intersection turn right to stay on the aqua-blazed Long Path.
In one tenth of a mile come to a 4-way intersection with the red-blazed Hang Glider Road. As the name indicates, this road leads to the spot where hang gliders and paragliders take off. You have a few of options here. If you are not comfortable following unmarked trails, you can proceed straight on Hang Glider Road to the views at the end and return to this intersection adding .6 mile total to this hike, then continue on the Long Path to High Point following the signs. You can simply skip the Hang Glider view and turn left to continue on the Long Path to High Point. Or keep straight on the red-blazed Hang Glider Road, enjoy the views, then look for a footpath into the woods on the left near the clearing at the edge of the cliff. Although this trail is not blazed, it is very well defined and relatively easy to follow along the rim of the escarpment. Watch your footing as the trail sometimes runs close to the edge and you need to step over fissures in the limestone rock surface. The more popular southern part of this park has fences and warning signs along the rim. None of that exists on this more rugged trail, so be careful!
Once on the unmarked footpath, keep left at the fork a short distance into the woods, then turn right at the T-intersection. In .3 mile keep right at a fork and keep right again at the next fork in another .3 mile. You will then soon emerge at an intersection with the aqua-blazed Long Path at High Point. Turn right to the High Point overlook where some large, flat rocks make nice seating for a break spot.
Retrace from the overlook back to the Long Path, which is combined with a red-blazed trail. Keep right on aqua/red when aqua/red also goes left. (The left side is where you would have arrived from had you opted to take the Long Path instead of the unmarked trail from Hang Glider overlook.)
Almost 2.5 miles into the hike leave the Long Path by turning left on white connector trail W3. When W3 ends at an intersection with the red-blazed Fred Schroeder Memorial Trail and connector trail W4, continue straight on red. Come up on an intersection with a cairn and directional arrows. Turn left here on connector trail W2 although you won’t know that is what the trail is until you turn around to see the signs behind you. (Connector trail W2 is shown as an unmarked woods road on the map instead of a white-blazed trail.) Keep left at an unmarked fork, then left on the yellow Perimeter Trail when white W2 ends.
The Perimeter Trail is a woods road that appears to be paved until you look closer and see that it is a rock slab surface you are walking on. The walking surface will alternate between smooth rock and gravel. Keep left at an unmarked fork, then continue straight uphill on yellow at the intersection with Hang Glider Road. Again continue on yellow when white connector W1 crosses over.
Four miles into the hike, a “Junction Ahead” sign signals an upcoming intersection that is not blazed. Keep right and you will soon find the yellow markers once more. In just a tenth of a mile from this intersection arrive at a pretty pond on the left with a bench on the right. Sit quietly on the bench for a few minutes and watch the pond come to life.
From the pond continue straight on the woods road. A footpath, also blazed in yellow, leaves to the right. This trail is not on the map. Continue straight on the woods road and yellow markers will come back into view. Keep left at an unmarked fork and arrive back at the parking area .15 mile from that last fork.
[ 0.00] From parking on Ryan Road, facing the kiosk and map box, turn right and follow yellow markers into woods on footpath at the park sign.
[ 0.10] Keep straight on yellow when a woods road crosses over
[ 0.20] Cross wooden footbridge
[ 0.35] At end of yellow turn left on aqua Long Path
[ 1.05] Turn right on aqua Long Path when white connector W1 goes straight
[ 1.15] At 4-way intersection, keep straight on red-blazed Hang Glider Road when unmarked goes right and Long Path goes left
[ 1.45] Hang Glider clearing with views; left on unmarked footpath into woods - after few steps keep left at fork then turn right at T-intersection
[ 1.75] Keep right at fork
[ 2.05] Keep right at fork along edge of escarpment
[ 2.20] Come out at intersection with Long Path coming in from left; right a few steps to High Point Overlook; retrace on Long Path; few steps ahead keep right on red/aqua when red/aqua also goes left
[ 2.45] Left on white connector W3 when aqua/red goes straight
[ 2.80] Straight on red at end of white connector W3 when white W4 goes right and red goes left
[ 2.95] At cairn with red arrow, turn left on white connector trail W2 (you need to turn around to see the sign)
[ 3.15] Keep left at unmarked fork
[ 3.25] Left on yellow at end of white W2
[ 3.55] Keep left at unmarked fork
[ 3.60] Keep straight uphill when the red Hang Glider Road goes left
[ 3.75] Straight on yellow when white connector W1 crosses over
[ 4.00] "Junction Ahead" sign; junction unmarked, keep right - yellow blazes continue ahead
[ 4.10] Pond on left, bench on right; continue straight on yellow
[ 4.15] At end of pond keep straight on woods road then straight when a yellow-blazed footpath (not on map) goes right
[ 4.30] Keep left at unmarked fork
[ 4.45] Back at parking on Ryan Road