Engagement Session

Capturing a Madison Square Park Morning Couples Session

A Romantic Madison Square Park Engagement Session

As a NYC Proposal and Engagement Photographer, I’m always eager to work in locations that blend genuine NYC charm, history, and meaning—and Madison Square Park is just that. Early in the morning, when the streets are calm, the park glows with soft, even morning light, perfect for photography. For this couples session, we chose Madison Square Park for its proximity to Eleven Madison, a restaurant with a ton of meaning to this couple. It’s where they went to celebrate their many professional accomplishments, and it’s where they got engaged! Naturally, we included the front of the restaurant in their photos.

Why Madison Square Park is Perfect for Engagement Photos

The beauty of early morning here is unmatched. The soft, diffused light highlights the park’s greenery, the surrounding architecture, and the calmness of the neighborhood before the city fully wakes up—capturing that unmistakable NYC charm while keeping the moment peaceful and intimate.

Whether you’re celebrating your engagement, planning photos for save-the-dates, or simply wanting to preserve this exciting chapter of your story, Madison Square Park, Gramercy to the East, and Chelsea just to the West offer the perfect blend of timeless New York elegance and urban romance.

Capturing Iconic NYC Moments

For this proposal, we started with the big moment framed by the greenery of Gramercy Park. After she said yes, we transitioned into an engagement session nearby. One of the most iconic shots of the evening? The couple emerging from the classic New York City subway entrance, the golden light streaming behind them, and yellow cabs zipping by—it doesn’t get more “New York” than that.

Planning Your Gramercy Park - NYC Couples session

If you’re considering an engagement session - couples sessionn Gramercy Park, here are a few quick tips:

  • Lighting is key and so are crowds — the park and surrounding streets glow beautifully in the morning light, and the park is the emptiest at this time of the day. While the late afternoon looks GREAT for lighting as well, the park is going to be busy and there will be a lot more people in your photos.

  • Mix in city energy — capture yellow taxis, subway entrances, and brownstones for iconic NYC photos.

  • Celebrate nearby — Gramercy and the Flatiron District are full of chic restaurants and cocktail bars, perfect for celebrating afterward.

Jonathan Heisler Photography is comprised of professional New York City photographers specializing in photographing private NYC proposals, as well as engagement sessions and weddings.