A Laid-Back Hiking Proposal at Ward Pound Ridge Reservation: A Westchester Proposal


There’s something really special about a proposal that feels completely true to a couple, and Jack and Domna’s day was exactly that.


On a crisp mid-March afternoon, Jack brought Domna to Ward Pound Ridge Reservation in Pound Ridge, NY for what she thought was just a casual hike. The plan was simple: spend time together outside, enjoy the trails, and bring along their dog, Nonna. Nothing about it felt out of the ordinary, which is exactly what made it such a perfect setup for a surprise proposal.


From the beginning, Jack was really intentional about making sure the proposal reflected their relationship. They’re both super relaxed, outdoorsy, and not into anything overly staged or flashy. A quiet hike together felt much more “them” than a big, public moment.


This was actually my first time photographing a proposal during a hike, which made it extra fun (and a little strategic). I stayed ahead of them on the trail, pretending to casually photograph the scenery so I wouldn’t raise any suspicion. There’s always a bit of a balancing act in moments like this as I am trying to be close enough to capture everything, but not so obvious that it gives anything away.


Then, at the perfect spot along the trail, Jack paused, turned to Domna, and got down on one knee. The moment felt so natural and intimate. No crowds, no pressure. Just the two of them (and Nonna!) surrounded by trees and that early spring quiet. Domna was completely surprised, and you could immediately see how much it meant to her.


After the proposal, we continued along the trail, taking portraits that felt just as relaxed and candid as the moment itself. One of my favorite parts was incorporating Nonna into the photos; she was the sweetest little addition and made everything feel even more personal.


What I loved most about this session was how unposed everything felt. They weren’t trying to create a perfect, picture-ready moment, they were just being themselves, and that’s what made the photos so meaningful.


During our time together, Jack and Domna mentioned they’re considering eloping instead of having a big wedding, and honestly, it couldn’t suit them better. Their relationship feels grounded, easy, and deeply connected--the kind of love that doesn’t need a big production to be powerful.


If you’re planning a proposal in Westchester and want something that feels private, natural, and meaningful, Ward Pound Ridge Reservation is such an incredible option. It offers so many quiet trails and scenic spots, making it perfect for couples who want a moment that feels like their everyday life but elevated in just the right way.

A couple shares a romantic moment in a wooded area by a stream while their dog watches nearby.
A couple kisses during their proposal on a hike in Westchester in Ward Pound Ridge Reservation.
A couple sits with their small dog by a river on a sunny day, surrounded by bare trees in Ward Pound Ridge Reservation after their proposal.
A couple sits on fallen leaves by a stream with their small dog while sharing an intimate moment in nature.
Close-up of hands with an engagement ring resting on blue denim fabric.
A couple sits together on a fallen log in the woods, wearing casual winter clothing and sharing a tender moment.
A dog's paw rests gently on top of two human hands wearing an engagement ring during a proposal in Westchester County, NY.
Two people sitting by the water looking at a phone together while wearing casual winter clothing on a sunny day.
A couple sits with their small dog by a stream in the woods on a sunny winter afternoon.
A couple embraces on a sandy riverbank in winter, sharing tender moments across multiple romantic poses.
A couple embraces by a river in winter, wearing warm clothing including a beanie and colorful scarf.
A couple embraces in a romantic moment outdoors in a wooded setting during a black and white photo session.
A romantic couple sharing a kiss outdoors by a stream, wearing winter clothing and a colorful patterned vest.
A couple shares a romantic moment during a marriage proposal in a winter forest setting.
A couple walks hand in hand with their dog along a wooded trail on a winter day, captured in black and white.

Thinking about proposing in Westchester or NYC? Let's chat.


Tell me what you have planned so far, and I'm happy to help fill in the details and photograph your big moment! Can't wait to hear from you :)