Issue #21 — Wednesday, October 7, 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.
In 1890, a group of investors set out to build the Dunderberg Spiral Railway — a scenic tourist line that would loop around the mountain nine separate times, climbing nearly 1,600 feet over roughly six miles of hand-cut grade, trestle ledges, and blasted stone cuts. Then the Panic of 1893 hit, the money vanished, and not a single train ever ran. The graded railbed is still there — wide, benched, and eerily deliberate underfoot — and today's hiking loop follows long stretches of it before breaking off to a rocky summit with a Hudson River view over Iona Island and the Bear Mountain Bridge.
A railroad that never carried a passenger, plus a river view at the top. That's two "wows" for the price of one trailhead.Start at the Jones Point park-and-ride on Route 9W, just south of the Bear Mountain Bridge traffic circle. Pick up the white-blazed Ramapo-Dunderberg Trail, which climbs quickly into the first stone cut — a narrow rock-walled passage that's an obvious, dramatic opening landmark. From there the trail keeps tracing the old railway grade in long, graded arcs, gaining elevation steadily rather than in one brutal pitch.
The hard part comes when the loop picks up the blue-blazed Timp-Torne Trail for the push to the summit ridge — footing turns to loose rock and short scrambles, and this is where sturdy boots (not sneakers) earn their keep. The payoff is the open ledge near the top: Hudson River views stretching past Iona Island to the Bear Mountain Bridge, with the old spiral grades visible switchbacking below you if you know where to look.
The descent follows a different arc of the loop back toward Jones Point, rejoining railway grade for the final stretch. There's no easy shortcut partway through — if anyone's running out of steam, the honest move is to turn back toward Jones Point before committing to the Timp-Torne climb, rather than push for the full loop.
Fifteen minutes north, Peekskill has a genuinely revived downtown and a Hudson riverfront to cool down at. Some easy hits:
Water (1.5L per person minimum), real hiking boots, layers, snacks, sunscreen, a small first-aid kit, and a phone with the trail map downloaded offline (cell service is patchy once you're past Jones Point).
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.)