A Day Trip: Jockey Hollow

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“There is wood I am in hopes sufficient for the purpose of hutting and firing...There is water in plenty tho it will be some distance to fetch”

A MORNING STOP

Before making our way to Jockey Hollow, we stopped at The Wicker Basket Deli in Mendham- a town with classic, colonial charm and a history as rich as its current culture. We were looking for some breakfast and a cup of coffee before we set out on our hike. We ordered one Taylor ham, egg, and cheese on a plain bagel and one bacon, double-egg, and cheddar, also on a toasted plain bagel...both with salt, pepper, and ketchup (of course) from a cheerful and

welcoming young lady who turned out to be one of the owners, Alexa. We sat on the bench outside and were completely shocked to have found some of the best sandwiches we have ever had. Mind you, we are not connoisseurs- foodies as they would be called today- but we take breakfast seriously, and when we tell you it was top-tier, you can take our word on it.

 JOCKEY HOLLOW

I have often wondered how different parts of the state must have looked in the past. It’s something I did even as a little kid. So often I would find myself thinking, “I wonder if people sat on this exact rock,” “I wonder if a kid ever lost his ball down here,” “Did they skip stones like this back then?” In Jockey Hollow we have the opportunity to walk in the very footsteps of those who fought to make this country what it is. And although the winter the Continental Army spent in Jockey Hollow was undeniably miserable, the quote above from Nathaniel Greene makes me wonder how many of the men encamped there couldn’t help but to love- if only for moments at a time- the beauty of that place.

  It was here, in the brutal winter of 1779–1780, that General George Washington chose to encamp the bulk of the Continental Army—more than 10,000 soldiers—as they endured what many historians agree was the coldest winter of the war, even harsher than Valley Forge.

The land, once owned by the Wick family, offered two strategic essentials: wood for shelter and high ground for defense. Soldiers used that timber to build over 1,000 log huts, forming a temporary city in the woods. Though food was scarce and morale was often low, not a single mutiny occurred that winter—a quiet testament to the grit of Washington’s men and the leadership of officers like Nathanael Greene, who oversaw supplies and camp organization.

 Today, it is a favored spot for hikers, bikers, dog-walkers, and at least one college student who used to spend breaks between his morning classes there. Despite its history, the beauty and stillness there are what make it feel so timeless.

From Mendham Borough, it was about 8 minutes to the main entrance of Jockey Hollow. Only a few cars dotted the main lot as we turned onto the tour road. We passed about a dozen hikers walking along the wide-smooth road before we parked in the lot near the Aqueduct Trail. Here we rolled down our windows and enjoyed our coffee in the dappled light. I won’t lie and say that it didn’t occur to us to just sit right there the whole time. But we set out from the lot first up the Grand Parade Trail, which is on the right side of the lot. It’s a wide, nicely mowed trail that brings you right into the woods. Mature hardwoods line the trail, and about 100 yards in, you can find some raspberry brambles which had quite a few ripe berries for the picking. The trail narrows slightly as it cuts deeper into the woods, and it was just wide enough for us to make way for two young guys hiking out passed us. As the going got a little rockier, we decided to turn back to the lot. There, we made our way to the opposite side and entered the Aqueduct Trail. There is a crystal clear stream that is crossed by a small wooden bridge as you walk into the Aqueduct Trail. The water is so cold and so clear that you just instinctively want to drink it, or, as the singer says, “I found the water so clear that I bathed in it”...we did neither, but it did occur to us! On through the trail we continued and something happened that tends to happen on walks like these: with every step, the “world” felt further and further from us. First, you forget the time, then the conversations you were having, then the emails you were waiting for, then the groceries you have to get, until you get to that point where you just are where you are. You feel the sun, the periodic breeze, the muscles in your legs, you hear the bugs and the birds, the scurrying and chirps of chipmunks, and gradually, without fail, if you do it for long enough, you feel refreshed, reconnected. When we came out of the trail and made our way back to the car, it somehow felt like we had slept: there was an undeniable break from all we had been doing and worrying about before we had set out. We sat for a little while by the brook at the entrance of the lot, had some water, and lingered a bit before we set off.

Sips and Shakes on Main Street

After our time in the park, we made our way back into Mendham Borough, strolling along Main Street until a cluster of cheerful orange umbrellas caught our eye. Beneath them sat Simple Coffee, a local gem with a warm, minimalist charm, a refined, full-bodied menu, and an owner who possesses the rare quality of seeming to enjoy their work.

We ordered two protein shakes and a chocolate chip muffin that looked too good to pass up while a patron worked on her laptop at one of the cafe tables. We settled in at the live-edge counter by the picture window and enjoyed our shakes—fresh, delicious, and surprisingly filling. Afterward, we shared the muffin (I’ll be honest, I ate most of it) that was hearty and satisfying, yet somehow not overly indulgent, even with its generous chunks of milk chocolate, as people filed in and out. Some were on breaks from work, some were on their way somewhere, some were returning home, some had kids in tow, and some had a paper tucked under their arms and showing every intention to sit and enjoy their coffee to the last sip. And watching everyone and every car pass by, I thought of all the people through all the ages, back to the 17^th century, that hurried down these same Mendham streets.

And I wondered again: Maybe they, too, paused right here and felt the simple joy of a day well spent.

If you have the time, we can't recommend this day trip enough...Do you have a day trip you would like to share? Let us know here