Issue #19 — Wednesday, September 23, 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.
The ridge above you is shaped like a giant lying on his back — that's not a metaphor, it's the actual reason the park is named Sleeping Giant, and once someone points out the "hips" and "knees" in the traprock skyline, your kids won't stop seeing him. Climb to the summit and you're standing on a fieldstone-and-timber observation tower built in 1936, a squat little castle with a turret staircase that pops you out above the treeline for a view over New Haven Harbor, the Yale campus spires, and Long Island Sound. Then you drive ten minutes into a city that claims to have invented American pizza, and you get to settle the argument yourself.
A geology lesson, a castle tower, and the apizza capital of the country in one afternoon. That's the bar for this newsletter.Park at the main Tower Trail lot off Mount Carmel Ave — it's well marked and fills up fast on fall weekends. From the lot, take the paved Tower Path, a wide, steady, stroller-friendly grade that climbs gently for about 1.5 miles through hardwood forest. This part is easy enough for younger kids and the natural turnaround if anyone's not up for more.
At the summit, the fieldstone tower is the reward — climb it if it's open (weekends and holidays, 9am–5pm) for the rooftop view. To make a loop instead of backtracking, pick up the blue-blazed Quinnipiac Trail along the ridge. This is the harder, more interesting half: it traces the giant's "hips," with rockier footing, short scrambles, and more up-and-down than the paved side, before dropping back down to the lot for a 4.2-mile total loop with about 700 ft of gain.
If anyone's running low on patience or daylight, you can always retrace the paved Tower Path back down instead of continuing onto the blue trail — it's less scenic but faster and easier on tired legs.
Ten minutes down the hill, New Haven has the Yale campus to wander and the country's best claim on inventing American pizza. Some easy hits:
Water (1L per person), sturdy sneakers or hiking shoes, a light rain layer given this weekend's forecast, snacks, sunscreen, and a phone with the trail map downloaded offline.
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.)