Surprise Proposal at Fishkill Farms | Hudson Valley Wedding Photographer

January 5, 2022
New York Surprise Proposal | Hudson Valley Wedding Photographer | Hudson Valley Engagement

Photographing a surprise proposal in the Hudson Valley, right in a nearby orchard? Done.

Upstate NY proposal photographer

I love orchards, and I love capturing surprise proposals in New York and beyond. So you can imagine that when William called me about proposing to his girlfriend right here in the Hudson Valley, I of course said yes (and no, I wasn’t being proposed to).

I’m a New York wedding photographer who was raised in the Hudson Valley, so a summer or fall trip to the orchard is always something I look forward to. This time, however, I had to pretend I was there picking nectarines…with 2 cameras.

Lucky for me, William decided to propose on a Saturday when there were just enough people for me to blend in. I was able to find them immediately thanks to our phone calls and planning. What made William stand out was just how darn excited he was to propose. He was so excited, he almost tripped over his words when describing the entire weekend he planned. First was the drive up from NYC, then lunch, then the proposal, and then dinner with a romantic stay at a bed and breakfast upstate.

William organized everything at Fishkill Farms, a well-known Hudson Valley orchard. More than just an orchard, they have a bar and farm store, live music, restaurant, and events, and offer everything from hayrides and flower picking to organic fruit and veggies you pluck from the vine yourself. Not your average small-town farm, Fishkill Farms is one of the largest farms (similar to the Hudson Valley’s equally-famous Barton Orchards at 270 acres).

How the Proposal Happened

Though William and Caroline had known each other for years and were on a local NYC board together, they didn’t start dating until they’d known each other for some time. And what immediately stands out about these two is their height difference. While Caroline is about 5’2” in heels, William is a solid 6’5”. So yes, one might say they were easy to spot.

It was supposed to rain in New York on the day William picked for his secret proposal, but we got lucky (unlucky?) and got boiling hot weather instead. I’m pretty sure all three of us were sweating through our clothing. All the same, the show had to go on! I tracked the two of them and pretended to be talking on the phone, and at the appointed time in a row of peaches and nectarines, he got down on one knee (which made him basically at her height) and asked her to marry him. I clicked away as she grinned and said yes.

Upstate NY proposal photographer
Upstate NY engagement photographer

Caroline may not look surprised during her surprise proposal, but for the next hour she kept saying she was in utter shock, and just couldn’t believe it.

But finally, I got a few shots of her looking in total disbelief at having just been proposed to. I love these two below!

Spreading News of Her Surprise Proposal

Guess what she did right after this swelteringly hot New York proposal? Video called all the family members she could, from right there among the trees.

She loved calling up her friends and family with William and then moving her new ring into view so she could hear the yells of congratulations. These are some of my favorite shots.

After a shirt change and cool down, we did engagement photos in the orchard, by the pick-your-own flowers, and by the hay bales.

They also did a cheers with local hard cider, and I got a ring photo on top of a freshly picked peach. All in all, it was a…wait for it…peach-perfect day.


If you love being outside and picking apples in the Empire [apple] State, doing your engagement photos in an orchard is a simple, fun idea. You can climb trees to pick fruit, set up a picnic, celebrate at the bar, or just get photos throughout the greenery of New York State (or any other state with photogenic orchards. I just happen to think New York wins this one. Not into the orchard scene (is there such a thing as one?!)? Not to worry. I have dozens of locations and ideas for your New York surprise proposal here.

Better shine than rain, this adorable, newly engaged couple lucked out with not a drop from the sky, and ended up with a gorgeous day to celebrate this surprise proposal in the Hudson Valley. I loved being there to photograph every moment of it!

New York Wedding Photographer | Upstate NY Wedding Photographer | Hudson Valley Engagement Photos

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Ah, what a sweet story! I love proposals, and you did a great job capturing it.

Oh my god! This is too perfect. They look so happy. You did such a great job! Proposal stories are so much fun to read. You did such a great job documenting their big surprise moment.

What a beautiful proposal! I wish more people would hire a photographer for proposals – they are so special. Her dress is gorgeous!

Your work makes such a strong case as to why couples should invest in a proposal photographer! Such heartfelt moments that will always be remembered!

So sweet! You captured their joy so well!

What a sweet proposal story and the perfect setting! Well done!

These photos are gorgeous, I love the colours!

these are so cute!!!! i love proposals – you did an amazing job capturing this!

Oh my gosh I love proposal stories!! You did an awesome job capturing their sweet story. 🥰