Issue #22 — Wednesday, October 14, 2026
One family-friendly hike within a 2-hour drive of Hoboken — plus where to take the kids to eat in the city and NJ. Hike it or skip it; either way your weekend's sorted.
You turn sideways and shuffle through the Lemon Squeezer — a boulder-walled crevice on the Appalachian Trail so narrow in spots (about 2 feet) that you'll want to hand your kid's backpack through separately before you duck under the overhanging chockstone. Thirty seconds later you pop out at "Times Square," the spot deep in the woods where four differently-blazed trails converge at a single wooden signpost — hikers have nicknamed it after the real one since the 1920s, because on a busy fall Saturday it genuinely gets that crowded. Along the way you'll skirt Island Pond, a glacial pond with an active beaver lodge, on a stretch of the A.T. that's been walked continuously since the trail's earliest days.
A slot-canyon squeeze, a goofy nickname with real history behind it, and a pond full of wildlife — three "wows" before lunch.Park at the Elk Pen parking area off Arden Valley Road, just east of the Route 17 Southfields exit — the field it's named for once penned an actual herd of elk New York tried (and failed) to establish in the early 1900s. Pick up the white-blazed Appalachian Trail heading north across that field and into the woods. The path is rocky and root-crossed almost immediately, so this isn't a stroller hike. Around 1.5 miles in, the trail runs along the shoreline of Island Pond, a glacial pond with open water views and the beaver lodge mentioned above. This is the natural turnaround for younger or less experienced kids — out and back, it's about 3 miles total.
If the group's still game, continue another mile or so to the Lemon Squeezer: a jumble of boulders that funnels into a narrow rock corridor you have to turn sideways to get through, finishing with a low chockstone to duck under. There's a short unmarked bypass around the squeeze itself for anyone claustrophobic or carrying a big pack — ask another hiker to point it out if you don't spot it, it's easy to miss. Right after, you'll land at "Times Square," the junction where the A.T., the Ramapo-Dunderberg Trail, and two other routes all meet at a single signpost.
Loop back south via the red-dot-on-white Ramapo-Dunderberg Trail, which winds through rolling oak forest back toward Arden Valley Road and the Elk Pen lot, closing out the 6.2-mile loop. The descent is gentler than the approach — no technical sections, just steady walking.
About 15 minutes from the trailhead, Warwick is deep in apple country in October. Some easy hits:
Water (1L per person), sturdy hiking shoes, a light windbreaker, snacks, sunscreen, and a phone with the trail map downloaded offline (cell service is patchy once you're past the Elk Pen lot).
Not feeling the drive this week? Here's where to take the kids instead — in the city and across the river. (No connection to this week's hike.)