Bear Mountain and Minnewaska State Park Engagement | Hudson Valley, NY | Jessie and Dan (and Jaime and Diggory)


This is a very special engagement session that I’m sharing today, because it’s my sister’s! I was so excited when Jessie called to tell me that Dan had proposed to her - while they were on vacation in Norway! How cool is that?! These two are always traveling and adventuring together, so it was the perfect addition to one of their many memorable trips. Jessie and Dan also love adventuring closer to home as well, and they’re out almost every weekend going on hikes with their dogs, Diggory and Jaime. We decided to hit up some of their favorite hiking spots for their engagement session!

Since I was planning a weekend trip up to New York, we decided to spread the shoot out over two days. Day 1 was at Minnewaska State Park with humans only, and Day 2 was at Bear Mountain with the pups included. These dogs are adorable, but they’re also big and full of energy! So we thought we’d have better luck getting some photos of Dan and Jess alone if we left the dogs at home for part 1 of the photos.

It was windy and freezing that first day, so we spent roughly 8 minutes at an apple orchard with Jessie wearing a dress haha. Then it was time for jeans and a sweater!

Oh Jessie, so happy striking this pose. She has no idea why I asked Dan to stand a few feet behind her….

At Minnewaska State Park, we found the prettiest stream just off one of the roads! We got there just in time as the sun was setting behind the tree line.

I asked Jess to give Dan a kiss on the cheek hahaha. Not an easy task with the height difference.

The next morning, we brought the dogs along! We went to Bear Mountain State Park nice and early, before too many other people were around. We figured it would be easier to keep the dogs’ attention without a lot of distractions, but then there were vultures. And those are much more fun to look at than a camera!

But we just had to open up a treat bag to get their attention!

I love this series of pictures… Jaime gets jealous/protective if you pay too much attention to Diggory, so he didn’t like it when Dan was getting kisses!


Dan is originally from Alabama and he is a huge Auburn fan. So of course Jessie, Diggory, and Jaime have acquired lots of Auburn attire as well! Jaime just didn’t want to wear his haha, but he rocked the orange collar and blue/orange leash.

We made our way up to the top of Bear Mountain (by the Perkins Memorial Tower) for some incredible views of the mountains and the Hudson River.

I can’t wait for their wedding next summer! Where I will NOT be the photographer, but will have maid of honor duties instead :)

Engagements, DogsMegan ReiComment