Jockey Hollow Opens Patio with Cannonball Wine Dinner

Since my very first visit back in 2016—when I was wowed by everything from pâté to rosé—Jockey Hollow in Morristown has maintained its status as a top restaurant in the state.

But it’s so much more than that.

Amidst its Italian Palazzo style architecture, Jockey Hollow Bar & Kitchen has quickly become our state’s “it” destination for fine food and wine, craft cocktails and first-class ambience. Looking back, it was easy to see why the restaurant occupying the Vail Mansion would become so successful. But it wasn’t just the restored 17-foot marble columns or nostalgic 15,000-square-foot space. It was everything restaurateur, Chris Cannon, and his staff curated—transforming each visit to the mansion into a truly one-of-a-kind experience.

Jockey Hollow

Smoked Fettuccine with clams, melted leeks, crispy potato.

There’s a reason I’ve chosen to celebrate my last three birthdays at Jockey Hollow. The spaces and menus within evoke a sort of refinement that’s both elegant yet energetic. Across three floors, Jockey’s four separate dining spaces offer their own unique ambience and menu—each room’s name indicative of its cuisine and vibe. But there’s also a fifth (sort of).

Serving as an extension of the Oyster and Wine Bar—Jockey Hollow’s main dining area—the month of May kicks off the opening of the restaurant’s outdoor patio, as it has for the past couple years. In classic Chris Cannon fashion, the restaurateur celebrated the season with another five-course Cannonball Wine Dinner among the Vail Mansion’s enchanting grounds.

Although I’ve been to Jockey Hollow more times than I can recall, my experiences were limited to late evenings or wintery afternoons. So it was ironically the first time I’ve had the pleasure of walking the grounds in broad daylight. And the transition from day to night on the patio is just another piece of the experience that makes Jockey so special.

Jockey Hollow

Braised Spanish Octopus with spring bean stew, fennel sausage, oregano, salsa verde.

The dinner was curated by Cannon himself with wine pairings for each course, including a surprise pairing with his personal favorite cigar imported from Nicaragua. The cuisine was highlighted by dishes that I feel truly embody the essence of what the restaurant offers. Particularly a triple cream grass-fed blue cheese from New Zealand, which was offered as our final course. Meaning “sky blue” in Maori, the Kapiti Kikorangi was served with fennel pollen, toasted walnuts and hibiscus rhubarb. The full-flavored cheese showcased a network of blue veins throughout and was paired with Domaine de Beaurenard Rasteau Les Argiles Bleu.

Also headlining the dinner was smoked fettuccine with clams, braised octopus with spring bean stew and (my favorite) a wagyu flatiron with bone marrow, creamed kale and porcini marmalade (paired with El Hombre Bala, a varietal Grenache from Madrid). Tasting the wines Cannon selected to complement each course was a reminder of how unpretentious Jockey Hollow really is. And interestingly enough, the best pairing of the night came from Gaia Wines’ Retinitis Nobilis, an inexpensive Greek wine with a dry and gentle flavor profile.

As I lit the cigar on the patio with the sun vanishing beyond the estate, it all became clear. In just a few years, Jockey Hollow has become a true cultural hub, a world-class culinary destination with an ambience that cannot be duplicated even by the likes of our Manhattan neighbors. Whether you’re celebrating an occasion (like me) or simply want to unwind after a long work day/week with a lively atmosphere, Jockey Hollow is calling.

PS weekday lunch is back from 12pm – 2:15pm!