Background you can feel free to skip: If you’d like to spend the day rubbernecking, but you don’t feel like visiting Manhattan, Undercliff/Overcliff is your spot. This pleasant, relatively flat 5-mile loop sends you (as you might have inferred from the name) under a cliff, but what you can’t tell from the name is that this place is a huge hotspot for crazy rock-climbing people. As you stroll along the wide Undercliff carriage road with a never-ending view to your right, you’ll also have ropes dangling to your left every few feet, with tiny little humans clinging to the rock face hundreds of feet above.
Undercliff Road is so nice, I’d considered writing this hike up as an up-and-back affair, rather than a loop. What a mistake that would have been. In the several years since I’d walked the Overcliff Road, I’d forgotten how nice the views are there, too, looking out onto the Catskills and smaller ridges in the Mohonk Preserve.
If you’re looking for a longer hike, you could make this into an 8- or 9-mile extravaganza, visiting the Mohonk Mountain House (with its Sky Top Tower, Lemon Squeeze rock scramble and beautiful lake) once you reach the junction with Overcliff Road.
I’ve done this before, since it’s the poor man’s way to visit the Mountain House, rather than paying the $20 per-person ($25 on weekends) fee there. It makes for a long day, though, and I’d only recommend doing that if you’re feeling really, really spry. I’ll assume you’re not doing that, but if you’re interested, I’ll point the way in the trail guide below and leave you to it.
The parking area for Undercliff/Overcliff is a jumping-off point for many of the most popular hikes in the Hudson Valley. If you’re coming on a nice weekend day, try to get here early (or very late in the afternoon). The large parking lot can fill up, forcing you to stalk someone back to their car so you can steal their spot, like it’s the mall at Christmas. (Sometimes they just put cones at the entrance so you can’t even come in, which is a bummer. If that happens to you, park in the Wawarsing Lot less than a mile away, towards New Paltz, just under that hairpin turn on 44/55. You can still access Undercliff Road from there, but you’ll have a ton of stairs to climb first.)
Once you find a parking spot, though, you’re in for a visit to one of the most awesome and unique places in the Hudson Valley, or anywhere else.
1. Walk to the far end of the parking lot, away from the guard shack and entrance. You’ll see a short trail that runs roughly parallel to Rt. 44/55. Take this trail until you climb the stone steps that bring you up to a large trail junction, with the pedestrian bridge that leads across 44/55 straight ahead (don’t cross the bridge).
If nobody was in the guard shack when you drove in, this is the spot where someone will be waiting to relieve you of your 10 bucks (per hiker) and give you your day pass.
2. From the top of the stairs, turn left toward the “Welcome to Mohonk Preserve” kiosk, which you’ll walk straight past to join the well-marked Undercliff Road.
3. In just a moment, you’ll get your first views (that didn’t take long, did it?) off to your right, looking over the scenic pull-off parking area that you passed on your way in, if you came from the east.
4. That’s really all the direction you need for the next 2 miles or so. Just keep wandering down the road (I’ve seen parents pushing strollers here, the road is so flat), gawking at the views to your right and the gorgeous cliffs (complete with crazy people) to your left.
5. Notice the chalk on every single possible handhold, and on some impossible ones, too. You know, if you feel like noticing that.
6. As the road leads away from the base of the cliffs, you’ll see several little trails leading back to the cliffs, which you can ignore, unless you’re one of the crazy people with ropes.
7. The cliffs get smaller and smaller until you’re walking down a regular woods road without views on either side. Hey! We’re spoiled. Give us some views!
8. Through the trees, on your right, you’ll just be able to make out the Sky Top Tower at the Mohonk Mountain House.
If you want to hike all the way up there (bringing your total to at least 9 miles for the day, including that large hill you’re looking at right now), you’ll get your chance in just a moment. Don’t try it unless you’re really sure that’s what you want to do, and you have enough provisions to do it. Your day pass doesn’t allow you access into the Mountain House, just onto the grounds, and it’s a long way back to the car from there.
9. It took me about an hour from the parking lot to reach the junction with Overcliff Road. There are a mess of other trails at this junction. See the map podium on the little bridge to your right for a clear picture of the trail structure here.
Optional reading if you’re considering a visit to the Mountain House: It’s 1.5 miles to the Mountain House from this spot, plus a steep climb (or optional rock scramble) up to the Sky Top Tower, so we’re talking an additional 3-4 miles roundtrip. If you want to do that, go ahead, but I might recommend just paying the entrance fee and checking it out some other day, unless you’re super hard-core and/or cheap. I’ve brought friends along for that entire hike, and we all enjoyed it, but everyone was ready to see the car about two miles before we saw it.
If you do venture off to the Mountain House, bon voyage (and I hope you have lots of water and snacks)! Look for the Red Trail leading up into the rocks at the far end of the lake (near the Mountain House) if you want to do the Labyrinth rock scramble leading to the Lemon Squeeze. That scenic scramble takes you up to the Sky Top Tower, or you can just stroll up the paved (then gravel) path from the lake to the tower. That paved path is the way you’ll come back down, no matter how you get to the top.
Have fun out there, and good luck! Retrace your steps to this trail junction when you’re done, and rejoin us sane people for the stroll down Overcliff Road to end your day of hiking.If you’re a sane person, stick with me and let’s head back to the car via the Overcliff Road.
10. Follow the signs to take an immediate left onto Overcliff Road (that is, a left if you’re coming from Undercliff Road, not from the map podium).
11. In just a few minutes, you’ll wander past some more cliffs. These would look awesome on any other hike, but you’re all spoiled now. Yawn.
12. Enjoy the view of the Catskills that opens up to your right. This view sticks with you for much of your return trip. The only minor disappointment on Overcliff Road is that you don’t get any views over the tops of the cliffs you’ve just walked under, as the name seems to imply. But the urge to complain quickly fades away as you take in the awesome views you get instead.
13. After 30 minutes or so, you’ll find yourself in some quiet woods again, sans views.
14. In about an hour (or more, especially if the toddler riding on your back kicks off his shoe and you backtrack for ten minutes unsuccessfully looking for it), you’ll arrive back at the kiosk where you started. (And if you’re the jogger who went out of his way to return the shoe to me on November 6, 2010, you are a super cool person. Thank you again.)Once you’re back at the kiosk, turn right and go down the stone stairs to head back to your car. Going to bring your climbing ropes next time?
Directions to the trailhead: From New Paltz, head west on Route 299. Follow 299 until it dead ends into Rt. 44/55, where you’ll make a right turn. Follow 44/55 past the hairpin turn under the Shawangunk cliffs and arrive at the West Trapps Trailhead parking area on your right. Turn into the lot, drive past the guard shack and try to find an empty spot. (The picture below was taken pulling out of the parking lot, so it’s the reverse of what you’d see coming from New Paltz.)
You can also get directions by checking out the Undercliff/Overcliff entry on the HiketheHudsonValley.com Google map.
Sorta nearby address for your GPS: The Mohonk Preserve Visitor Center’s address is:
3197 Route 44/55
Gardiner, NY 12525
From there, just keep heading west on 44/55 for another 1.3 miles to find the West Trapps Trailhead parking area on your right.
GPS coordinates of parking area: 41.73677, -74.19865 (Clicking will open in Google Maps or the Apple Maps app, depending on your browser/device.)
Related resources: If you’re looking for actual facts and/or useful information, visit these resources:
Want to support trails in the Hudson Valley? Here’s one great way: Visit the New York-New Jersey Trail Conference homepage and click on Volunteer, Donate, or Shop! (Then you can volunteer, donate, or shop, depending on your mood.)