Brittin & Caleb | A Winter Proposal in Colorado Springs

colorado springs, co

You guys. This is maybe my favorite shoot EVER because I got to help my future brother-in-law ask my sister to marry him!!! Caleb called my husband Isaac and I about a month before he was supposed to fly out to Colorado to spend Christmas with our family, and he let us know that he was going to pop the question. No big deal. Just my emotions forever tied to a winter proposal on a mountaintop. 😭❄️

Isaac and I got to serve as his faithful location scouts, secretly Facetiming him with different location possibilities. His only requirement was simple and extremely reasonable: it had to be epic.

why winter is a beautiful time to propose

Winter proposals in Colorado are bound to be magical because, well, winter in Colorado. And proposals. Need I say more?. The crowds thin out and the landscapes somehow look even bigger and more dramatic. After several FaceTime scouting sessions and a few “okay but WHAT about this spot” debates, we landed on the top of Palmer Park. High up, wide open, snow-dusted, and some truly epic mountain views. It checked all the boxes.

Once the location and date were locked in, all that was left to do was wait. Which turned out to be the hardest part!

photographing a winter proposal

When Saturday morning finally arrived, Isaac and I hopped in the car and drove up to Palmer Park about forty minutes early. We needed time to get into position. Between my camera, Isaac’s very bulky video setup, and our plan to hide in literal bushes, we looked… suspicious. Every car that crunched up the gravel road sent our hearts racing. My parents were hiding in the bushes with us, making us even more inconspicuous. We squinted through bare branches trying to see if it was them, silently wishing I’d thought to track Caleb’s location like a normal person.

Then we heard it. Gravel popping. A car slowing. And suddenly there was Caleb, opening Brittin’s car door.

IT. WAS. HAPPENING.

They walked over to a picnic table overlooking the view and sat for a few minutes, totally unaware that half their family was crouched nearby. After a bit, Caleb took Brittin’s hand and led her toward the edge of the rock. Isaac and I went into full stealth mode, snapping photos from behind and praying she wouldn’t hear our camera shutters or our feet on the rock.

And then… he dropped to one knee.

He pulled out a ring (a stunning one, might I add). Brittin covered her face. And she said YES.

At that point, all professionalism was out the window. Isaac and I — along with my parents — burst out of the bushes, cheering, crying, laughing, and absolutely ruining any chance of subtlety. Brittin’s face when she realized we were all there is something I’ll never forget.

We wrapped things up by heading to The Broadmoor for dessert to celebrate, because honestly, how do you not? And just like that, my baby sister was engaged. I’m not crying, you’re crying. (Okay, fine, I’m crying.)

This day is a big reason I’ll always have a soft spot for winter proposals. There’s something incredibly intimate about them. The quieter parks, the crisp air, the anticipation of the holidays, the way couples naturally snuggle a little closer — it all adds to the moment. Winter also gives proposals a sense of intentionality. You usually don’t accidentally end up on a snowy overlook. You choose it. From a photographer's perspective, winter proposals in Colorado Springs are seriously underrated.