November 12, 2020

John & Caitlin | Shenandoah Mountains, Virginia Engagement Photographer

I’m Stephanie, a wedding + lifestyle photographer based in Colorado Springs, Colorado and Warrenton, Virginia. Whether I’m by the mountains of Colorado or Virginia, my soul feels at home, surrounded by rural living and the raw beauty of nature. I genuinely love what I do, and feel so passionate to share the enthusiasm and joy of these celebrations with you!

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John & Caitlin | Shenandoah Mountains, Virginia Engagement Photographer

You might think to yourself as you go through these photos, “are John and Caitlin models?!” Well, from our conversations, that is not their main profession, but I never asked if they did it as a side gig!! 😉 Haha! When John and Caitlin reached out to me, I was… A) Excited that I was available for their 2021 wedding day. B) Excited to photograph at Early Mountain Vineyards again! C) Be the photographer who would photograph their engagement in the gorgeous Shenandoah Mountains of Virginia!!!

As we briefly got to know each other via email/social media, I could hardly wait to meet them in person!! Oh, and we cannot forget their large fur baby, Oshie!!! The enthusiasm from this crew just had me on cloud nine throughout the entire session and afterward! And the perfect fall outfits to end the session with one colorful view really made my heart sing joy! Although, I love so many black and white photos too because they rocked both color and the classic B&W shots!! Caitlin’s smile just beams through these photos and I can only imagine how much bigger it can get next year when she marries her best friend. <3 I cannot WAIT to step back behind my camera again next year and photograph this sweet, fun, photogenic couple!!!

Also, be entertained by the cutest Saint Bernard photos below!!! Oshie rocked this session. Clearly, there was some practice for the camera before this session because … #modelstatus!!! <3 HAHA! I love photographing a good ole’ big, drooly pup! 🙂

John & Caitlin | Shenandoah Mountains, Virginia Engagement Photographer

John and Caitlin’s Love Story


from Caitlin’s perspective

The first time I saw John, he was wearing a grey sweatshirt and sweatpants combo, sitting on the couch watching football. I had heart eyes but was too nervous to talk to him at the time. A couple of months went by, and he friended me on Facebook. I thought, “Wow, did he actually notice me when we were in the same room together, and only a few minutes?!” My birthday came along in December, and he wished me Happy Birthday on my Facebook wall. In my mind, I thought if I only “liked” his birthday wishes, maybe he would get the hint. Spoiler: He did not. 

A few months go by, and we started to chat via Facebook messenger and set up a date. We then went on to meet up at a bar with a few mutual friends and family to watch a Washington Capitals playoff game. Now, if you know me, this is the highlight of my year and also my most emotional. Que tea on deck for the next morning because I usually lose my voice screaming at the tv.

Now, this important because if John ever told you he didn’t know what he was getting into, he would be lying. 😉

John and I both agreed to take tequila shots every time the caps scored. A little tipsy between periods, we stepped outside, and I grabbed his face and kissed him. This is not typically my style, and if anyone were to ask, I would tell them that it was all John. As John says, love is love. It was at that moment that I think that we both knew.


from John’s perspective

The Plan.

Proposing to Caitlin was the best night of my life. I knew from the day I met her that she was the one. From the moment I met Caitlin, two major things I learned very fast about her… 1) She LOVES Disney World. 2) She LOVES the Washington Capitals Hockey. I knew I wanted to incorporate one of those things for when I popped the question, and it just so happened that we were going to Disney World in November. It was perfect timing, and I had to pull it off.

There isn’t a place in the world that is more magical, that puts the biggest smile on her face, or that she would rather be. Anyone who knows Disney World, November through the holidays, they go all out at Magic Kingdom with their Christmas decorations. She absolutely loves it. They have a giant Christmas tree, reefs, ornaments, lights, and fireworks everywhere throughout the park. I knew I wanted to propose right on Main Street in front of the Cinderella Castle while the fireworks went off in the background! 

Getting to that point was a lot tougher than I thought it would be. Getting the ring through the airport security and Magic Kingdom park security without her knowing was enough to make you sweat. Spending 4-5 hours in the park without her knowing the plan was brutal (I wanted to put that ring on her all day!) It was all I thought about for months.  We spent the day walking around the park, trying the different foods and cocktails. I pushed us to drink more than we usually do, which I think she found curious, but we love to have a good time there, and that’s exactly what we did. Her parents were going to be there to surprise her after the proposal as well. (she gets her love of Disney from her mom, Pat).

“The Greatest Night of My Life.”

Once the sun went down, we made our way back to Main Street in front of the Cinderella Castle to catch the Christmas parade and fireworks. To set the scene — a giant gorgeous Christmas tree was at one end of the street, and at the other end was the castle. Caitlin’s parents hid behind the Christmas Tree (a story for another time… haha!) while I got a Disney photographer to snap some pictures of us in front of the castle. As the photographer was taking pictures of us, I got down on one knee and proposed just as fireworks were going off. It was perfect, and she SAID YES! Christmas music was playing, crowds of people cheered, and it really was the greatest night of my life. A night I will never forget.


Thank you, John and Caitlin, for giving me the GREATEST honor of being your engagement photographer in Virginia ‘s beautiful Shenandoah Mountains!!! Not only are you two as sweet as can be, but also fun and SUPER photogenic! Oh, I am so counting down the days until I get to hang out with you again and photograph your wedding day. <3 I know it will be the “greatest night of your lives!” So happy for you all!!!

Stephanie Messick Photography, LLC is a Florida Panhandle Beach Family, Wedding, and Engagement Photographer, also serving Northern + Central + Shenandoah Mountains, Virginia. Learn more HERE or contact her HERE and ask about the Destin, Florida Portrait Photographer Special if you’re visiting! Or contact her for information when she will be in Virginia for weddings/sessions!



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