Bear Hill Preserve & Grapefruit Squeeze


This hike is a hidden gem. Maybe because it’s hard to find and maybe because there’s just not much information about it online. Regardless, Bear Hill Preserve is an easy, kid-friendly hike to a dramatic cliff with panoramic views and the less well-known Grapefruit Squeeze – a relatively deep crevice of fallen boulders to explore that’s worth a visit on its own merits. It’s got a small parking lot, but the place is still largely under the radar, especially compared to the immensely popular Sam’s Point right next door.

Important notes

1. The hardest part of this hike is finding the parking area. This is not an exaggeration. Many, many people have gotten lost trying to find this place. Most online map sites and GPS apps have the wrong location. Please do not type “Bear Hill Preserve” or even the address into the search and blindly assume you’re going to the right place. You’re probably not.

2. Bear Hill Preserve is private property. Cost of admission to is $7 per person, (children under 12 free), payable by cash or online with PayPal.

Hike Length: 1.3 miles

Elevation gain: +180 feet

Location: Bear Hill Nature Preserve, Cragsmoor, NY

Bear Hill Preserve Parking

Directions: From Pine Bush, NY, drive west on NY-52 W for 7.5 miles. Make a sharp right onto Cragsmoor Road, then continue for 1.5 miles. Turn left onto Dellenbaugh Road, then immediately after turn left again to stay on Dellenbaugh Road. After 0.3 miles, the parking area will be on the left, just before the road makes a sharp turn to the right.

The official address is 117 Dellenbaugh Road, Cragsmoor, NY, 12420, but do not assume that entering this address will take you to the right place. In fact, it is likely to take you down roads that lead to private properties on the wrong side of the hill.

Trail Maps 

Bear Hill Preserve Map (modified from NY-NJ Trail Conference Shawangunk Trails Map #104)
Bear Hill Preserve Map (on the kiosk)

Bear Hill Preserve Trail Description

From the parking area, head towards the kiosk and pay the entry fee.

Bear Hill Preserve Kiosk

Walk past the kiosk and head towards the the Bear Hill Nature Preserve sign and the start of the trail, which appears to be an old road. The trail is not blazed but is easy to follow. There is one “Main Trail” and another “Old Trail” segment as well as the “Cliff Trail” leading to the cliff.

Just beyond the sign are a set of boulders designed to keep vehicles out. A plaque on one of the boulders honors the founders and past presidents of the Cragsmoor Association.

Just beyond, the relatively flat, level trail crosses a few drainages and wet areas on boards.

Just beyond, a house is visible on the left.

At 0.3 miles, you’ll pass a trail on your left to private property, marked with signs warning you to keep out. The trail then reaches a junction with the “Old Trail” which heads off to the right. We’ll take this trail on the way back, but for now continue straight to follow the “Main Trail”.

Sign marking Main Trail and Old Trail

The trail begins a slight climb.

It then reaches a “Do not Litter” sign and a junction where the “Main Trail,” “Old Trail,” and “Cliff Trail” meet.

Make a left at the sign to follow the “Cliff Trail”. A short distance further, the trail reaches its end.

Bear Hill Cliff & Vista

Here you reach a bright white rocky cliff with panoramic views. There are plenty of areas to explore here – be careful.

That’s not all! There’s more to explore up here!

From here, there are several small footpaths through the woods that you can explore, including a second area with a viewpoint, albeit a little less limited.

Grapefruit Squeeze

Before you explore further, one of the paths leading away from the cliff crosses a crevasse. Head down into the crevasse – called the Grapefruit Squeeze – and explore. This crevice in the rock cliff features a few narrow passages between fallen boulders and slabs suspended above you. It’s a fun, mild spelunking experience.

At the end of the crevice, you’ll reach an area with some large boulders and signs indicating “Private Property Beyond This Sign”. That’s a good hint to stop and turn around.

Walk back up the crevice, and then make a right down the foot path to explore another area of Bear Hill.

After you’re done exploring, follow the footpaths back to the main trail. Head down the Cliff Path downhill. When you reach the “Do Not Litter” sign and junction, you could return the way you came by turning right onto the Main Trail or proceeding straight to take the “Old Trail”.

Trail Junction.

We’ll continue straight along the Old Trail.

It’s a nice, level trail for the most part. Near the end, it makes a sharp bend to the right as it narrows and descends before once again connecting with the Main Trail. From here, turn left and retrace your steps back to the parking lot.

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