Tucked into the historic heart of Morristown, New Jersey, Jockey Hollow Bar & Kitchen set the stage for Anthony & Shawn’s engagement session that felt equal parts timeless elegance and modern romance.

*Update as of 3/9/26: We’re so sad that the restaurant is currently closed! But we’re hopeful they are changing hands and will be under new management soon!

From craft cocktails to golden hour strolls, this November session was such a blast from start to finish! These two enjoyed making martinis together in one of the bar areas, sharing plenty of laughs in the process.

After crafting the perfect cocktail, Shawn & Anthony wandered through the various rooms in the historic building. The marble staircase felt regal and timeless, while the red couch and old-school posters of another area brought a vintage-aesthetic, making for an incredible variety of backdrops. Inside one of the iconic dining rooms, soaring palladian windows flooded the space with natural light.

After soaking in the refined atmosphere indoors, we stepped outside to take advantage of Morristown’s picturesque surroundings. Just beyond the restaurant, tree-lined paths and manicured greenery offered a stunning background. As the sun dipped lower, golden light wrapped around them, illuminating their smiles and highlighting the changing leaves of autumn. Hand in hand, they strolled along the reflecting pool, occasionally glancing back with expressions of laughter and love.