Mike & Madison's Proposal at Pier 57

Mike and Madison got engaged on a sunny Saturday evening on the Pier 57 rooftop in Chelsea, a spot they'd walked past dozens of times since moving to the neighborhood. Madison had an inkling of suspicion something exciting may have been happening that day, but she did not expect the evening of surprises that Mike had in store for her!


How They Met

Mike and Madison met during their senior year at Villanova. They graduated, moved to New York together, and have lived here ever since, five and a half years in by the time Mike proposed just blocks from their apartment.

Man proposes to woman on rooftop terrace of Pier 57 in Chelsea with NYC skyline and One World Trade Center in background at sunset.

The Proposal

The plan, as far as Madison knew, was a relaxed day together. Mike suggested checking out the Pier 57 rooftop since it was close to home. He walked her straight to the railing where we'd planned the moment. The second he started proposing, she dropped her bag and phone and started crying and jumping up and down before he'd even gotten down on one knee. It was as unfiltered a reaction as I've photographed, and I absolutely loved it. They were both emotional, so excited, and some nearby viewers clapped for them, too!


After the proposal, I introduced myself and congratulated the newly engaged couple, then we took lots of portraits on the rooftop. Mike and Madison were so happy together and comfortable that they barely noticed me behind the camera as they just took in the moment. After some time, we guided Madison back to where they had just gotten engaged and both of their families appeared. As their families congratulated them, the hugs and tears started all over again.


The day wasn't finished yet, though! Madison thought dinner afterward was just family. Instead, she walked into a full engagement party with everyone closest to them already there waiting. The shock and joy on her face was equally matched with the energy of the party as everyone started greeting them! What an incredible way to finish off a proposal evening!


Couple dancing a romantic dip on a wooden deck with the New York City skyline in the background on the rooftop of Pier 57.

Planning a Proposal at Pier 57

If you're planning on proposing at Pier 57, head to the top level of the rooftop, up the wooden stairs, to the section under the large white canopy. It's quieter than the lower deck, has one of the better skyline views on the pier, and works well for sunset photos. Since it's covered, it's also a safe bet if rain is in the forecast. Pier 57 itself has restaurants and things to do before or after, useful if you're building a full day around the moment the way Mike did.

Man kneeling to propose to woman on rooftop deck with NYC skyline backdrop.
Couple sharing a marriage proposal moment on a rooftop deck with NYC skyline and One World Trade Center in background.
Man proposes on one knee with ring box on rooftop terrace with NYC skyline and One World Trade Center backdrop.
Man proposes on rooftop with NYC skyline backdrop, woman reacts with surprise and joy during romantic engagement moment.
Couple embracing on rooftop terrace with stunning New York City skyline and One World Trade Center in background.
Couple kissing on a rooftop deck with NYC skyline and Hudson River in the background on a sunny day.
Man presenting engagement ring box to woman on rooftop with NYC skyline backdrop.
Couple sharing romantic kiss on waterfront deck with city skyline behind them.
Couple sharing a tender embrace on a waterfront deck with city skyline and blue sky in background.
Couple sharing a romantic lift embrace on a rooftop deck with NYC skyline in background.
A couple shares a romantic kiss outdoors with a city skyline in the background on a sunny day.
Diamond solitaire engagement ring in red wooden box with NYC skyline background.
Man placing engagement ring on womans finger on a sunny waterfront pier with city skyline backdrop.
Close-up of a man placing a diamond engagement ring on a woman's finger with city skyline in background.
Happy engaged couple posing together on rooftop with NYC skyline and Hudson River.

FAQ

Where's the best spot on Pier 57 to propose?

The upper level, reached by the wooden stairs, under the large white canopy. It's quieter than the lower deck and has a strong skyline view.

Is Pier 57 a good option if the weather isn't cooperating?

Yes, the upper canopy area is covered, so light rain doesn't rule it out.

Is there anything to do at Pier 57 before or after a proposal?

Yes, the pier has several restaurants and food hall options, good for a low-key celebration right afterward.

Planning your own proposal at Pier 57?


If you're picturing a moment like Mike and Madison's, I'd love to help you plan it. I'm a proposal photographer working across NYC, Westchester, and the Hudson Valley, and rooftop spots like Pier 57 are some of my favorites for that skyline backdrop and golden hour light. Reach out and tell me about what you're planning and when you're thinking of proposing, and I will get back to you within 24 hours!