An engagement session at the Cornish Estate ruins in Cold Spring

Chelsea wore a dress for her engagement session at the Cornish Estate ruins, paired with a pair of practical Converse sneakers, since the fastest way in is still about a mile of trail.

Chelsea grew up traveling out to the Cold Spring area from western Connecticut, and the Cornish Estate trail became one of her favorite hikes along the way. She and Dan are both into hiking and like doing it together, so building their engagement session around a hike wasn’t a stretch for them, it was just what they already do.

It’s a trail I know well myself. Cornish Estate is one of my wife Adriana’s and our dog Toby’s favorite hikes too, since it’s flatter than a full summit climb but still rewards you at the end: a view of Storm King across the river, and the ruins themselves to explore.

Photos by Matthew Rigby Photography

Doing something that already felt like them

Chelsea and Dan describe themselves as “not picture people.” Building their session around something they already loved, rather than a new place or a standard engagement session location, made the whole afternoon feel fun and relaxed instead of like a performance. That’s usually the difference between a session that feels like work and one that feels like a good afternoon together.

As Chelsea put it afterward: “Our engagement shoot in Cold Spring was a great way to get to know each other and ‘break the ice’ before the big day. We were comfortable being ourselves around him, and spent a majority of the time laughing.”

Photos by Matthew Rigby Photography

A full circle moment

Later that year, Chelsea and Dan eloped at Kent Falls State Park in Connecticut, with their ceremony in front of the waterfall itself, surrounded by their immediate families and Dan’s two kids. After the ceremony, we hiked a short distance up to a viewing platform overlooking the falls together.

Looking back, their engagement session at Cornish Estate wasn’t just a nice backdrop. It set the tone for the rest of their story: hiking, family, and doing things in a way that felt like them rather than a template.

Cornish Estate is reached from the same trailhead as the climb up to Bull Hill, just a flatter, shorter route if you’d rather skip the summit. For more Hudson Valley locations, see my full engagement session guide.

Photos by Matthew Rigby Photography

Planning your own session here

If a hike feels more like you than a studio session would, I’d love to talk about what that could look like for your own engagement photos in the Hudson Valley.