A surprise proposal on Washburn Trail in Cold Spring, New York

Mary and AJ had been preparing for a three-day backpacking trip through the mountains of Hawaii, carrying everything they’d need on their backs. Before that trip, they wanted to test their gear with a practice hike closer to home. On a clear morning, they took the eight a.m. train from Grand Central to Cold Spring, walked from the station to the Washburn Trail trailhead, and started climbing.

Photos by Matthew Rigby Photography

The hike to the overlook

About a mile up the trail, the Hudson River opens wide below you. The view stretches from Little Stony Point, over the rooftops of Cold Spring, to the mountains of the Hudson Highlands in the distance. Mary had been thinking about this spot for two months.

When they reached the overlook, Mary asked AJ to stand still so she could take a photo. AJ posed with their back to the view, positioned with the morning light coming down through the trees, just as Mary and I had planned. She had thought through every detail in advance, including where to set down their fully packed backpacks so they wouldn’t be in the way and the two of them could move freely.

Photos by Matthew Rigby Photography

The proposal

AJ was still posing when Mary got down on one knee, pulled the ring from her pocket, and proposed.

AJ had no idea this was the day. Even though the trip required serious planning and coordination (Mary had even convinced AJ to skip the usual carbo-load pasta dinner the night before, since they had reservations at an Italian restaurant in the city that evening), nothing had given it away. I had been in place before they arrived, keeping the viewpoint clear as a few families passed through, and AJ had no idea I was there until it was over.

After Mary proposed, AJ proposed back. Mary had carried both rings up the trail in her backpack, because they had planned to propose to each other on the same day, AJ just didn’t know when. They stood together at the overlook for a long time, taking in the view and their excitement.

Photos by Matthew Rigby Photography

Engagement photos

We hiked on from the overlook toward a second viewpoint, looking north along the Hudson toward Storm King and Breakneck Ridge, and documented more photos there. Rather than backtracking the way they came, Mary and AJ chose the shorter loop down, which brought them past the Cornish Estate ruins on the way back to the trailhead. Their backpacks were part of the photos throughout, a real part of who they are and what this day was about.

Photos by Matthew Rigby Photography

Planning a proposal like this one

Planning like this is what makes a longer proposal package worth it. Mary and I had talked through the logistics in advance, such as the direction of the light at that time of morning, where AJ should stand, how to handle the backpacks in the frame, and how to keep the spot clear without tipping anything off. That preparation meant that when the moment happened, there was nothing to manage. We had time and space to hike together and enjoy the moment, sharing stories and laughs, rather than stopping coverage after the proposal itself.

If you’re planning a proposal in Cold Spring or anywhere in the Hudson Valley and would like to talk through what that could look like, I’d be glad to hear from you.

Worth knowing if you’re planning your own hike here: Washburn Trail leads up toward the Bull Hill summit, and about two-thirds of a mile in, the trail forks. Continuing straight takes you the rest of the way up to the summit and back the way you came. Turning onto the loop instead takes you past a couple of the best viewpoints on the mountain, then down past the Cornish Estate ruins before looping back to the trailhead, which is the route Mary and AJ took on their way down. For more Hudson Valley locations, see my full engagement session guide.