I highly recommend you purchase the New York - New Jersey Trail Conference map here. There are a lot of trails in Harriman State Park and not only will this map not get you lost, you can also change my route and add/remove trails.
Dec 30, 2018 — Starting from Silvermine Lake, walk along the Menomine Trail (yellow blaze) up to William Brien Memorial Shelter, then hop onto the Appalachian Trail (white blaze) / Ramapo - Dunderberg Trail (red blaze) and follow the A.T. as it veers north after less than a mile. The A.T. crosses Seven Lakes Drive before heading up Stockbridge Mountain and abruptly heading southwest. Keep your eyes peeled for an unmarked dirt road on the right that takes you to the Long Path (green blaze). The Long Path parallels the A.T. back up Stockbridge Mountain before passing a boulder named "Hippo Rock" and arriving at the junction with the Menomine Trail (yellow blaze). You could just take this trail back, but I wanted to get a little more elevation gain in, so I continued along the Long Path past the Stockbridge Shelter and down to a rock formation called "Cave Shelter". A slightly obscured dirt road leads you down to the Menomine Trail (yellow blaze), which leads back to the trailhead. A thing to note: on my 2016 map, the "Cave Shelter" is mislabeled as appearing after the dirt road, but it is in fact before the dirt road, and the dirt road is a bit more difficult to find than anticipated.
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