Location: Brewster
Distance: 2.75 miles
Skill Level: moderate
Elevation Gain: 350′
Type of Hike: loop
Trail Condition: gravel, dirt, rocky
Wow Factor: large boulders
Note: very poorly marked

How to get there: From I684, head east on 312.  At a bend in the road, you will see flashing lights for the rail road tracks.  Ice Pond Road is just before the tracks.  Turn left on Ice Pond Road.  Follow it down about a mile.  The small parking area is on the right.  If you hit the dirt road again or Tommy Thuber Rd, you went too far.

 

Summary: Head around the chain on the road to the right of the parking area.  Follow this large, gravel road downhill.  You’ll pass an unmarked trail to the left and keep going.  Almost to the bottom, the road will switch back right and a trail will head left (you could just turn left if you didn’t want to go to the bottom).  It is just about half a mile down to the bottom.  There are a few foundations on the way.  The area right around the ice house can be muddy.  There is a sign saying stay off the live rail road tracks but peek through the split in the fence and check out “Ice Pond” where they would go collect ice in the winter.  You could take a stroller and make an out-and-back mile.

Head back up to where that second trail split.  It is very badly marked blue.  You’ll have a steady climb, parallel with Ice Pond and the rail road track.  If you’re lucky (or really slow like my toddler) you may get to see the train.  Views may be seasonal.

You’ll also pass some really incredible and large boulders.  Rock climbers come out here to go bouldering and you can see the chalk marks on some of the edges.  There is a fork just past the first boulder.  Keep right.  I believe they meet back up at the second one but I’m not positive.

About 1/3 mile from the split off the road, the trail loops back in the opposite direction.  Keep your eye open for those faded blue markers in spots where the trail follows exposed rock over dirt.  The top of the hill starts to have some trails that veer off to nowhere or circle you back around.

The top of the hill has nice views but some may be seasonal.  Some unmarked trails head out to cliff edges so be careful if you have little walkers.

You’ll come to a pine tree with a large boulder half buried under it.  The trail splits around this and can be difficult to follow.  Head right and enter the clearing with fire pit remnants and lots of broken glass.  Cross to the far corner and pick up the blue/white trail that will take you down.

Follow blue/white for a while.  Take white left.  Blue will head right and will rejoin a little further down the hill.

Follow blue/white until you come to a T intersection.  Go right on the unmarked trail.  Blue will head uphill to the left.  Follow the trail down and head right on the larger unmarked road.  Keep following this road right until you come to Ice Pond Road.

Left on the road and head about half a mile back up to the parking lot.

 

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