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Jockey Hollow Preserve Trail

Jockey Hollow Preserve Trail

It was literally, technically and absolutely freezing cold the day we journeyed through Jockey Hollow – all the better to empathize with the soldiers who huddled here long before we did. Replicas of soldiers’ huts atop the hill demonstrate accommodations for the Continental Army during the harshest winter of the Revolutionary War.

We hiked back down the hill past the Grand Parade, where soldiers met for inspection, to receive their orders and to witness executions. From here we took the yellow trail to the orange, which swept us through a gorgeous, broad forest, to the perfectly picturesque meadow where the Wick house sits. After picnicking on the sun-drenched stoop beside the kitchen garden, we followed the yellow trail, which parallels the road, back to our parking spot. To our huge delight, we shared the trail with a plump fox, a family of deer and a woodpecker.

There is an amazing concentration of preserves and trails in the area – and connecting trails could keep you walking for days. Notably, the 46-mile Patriot’s Path runs straight through Jockey Hollow.



There are 4 parking lots from which to set off. We chose the one closest to the soldiers huts – but our loop took us past all of them.


A Zinfandel – because it’s so robust and spicy and bold.

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