48 Hours to Propose in Aspen

Surrounded by acres of wilderness and blessed with nearly 300 days of sunshine per year, this former mining town is an adventure seekers dream come true. I figured, what better way to set the tone for our life together than with a weekend filled with the proper balance of outdoor activities, delicious meals and a few celebratory glasses of wine?

Despite summer being the ‘other peak season’ for Aspen, we were fortunate to secure reasonable flights right into town. The proposal stage was set. The plan was in motion. Look out Aspen, here we come.

2-Hours To Go: It’s Go Time

After countless hours of research prior to this trip, I decided to get down on one knee at the half-way point of a horseback riding trip in the Elk Mountains just outside of Aspen.

Before we set out, I triple checked my backpack for my camera, iPad, headphones and, most importantly, the ring, and and we headed out for a day in the mountains. My nerves were getting out of control as we arrived at the trailhead to meet our jovial guide, Emily. 

She greeted us warmly and introduced us to our beautiful horses. While it seemed like a perfect day to get out in the fresh mountain air, she mentioned that there were rain jackets available for us…just in case. “If you don’t like Colorado weather,” she pondered while looking up at the dark clouds rolling in, “just wait five minutes.” 

All smiles, the three of us set out on the trail. Jessica had no idea what we were in for. And as I was very quickly to learn, neither did I.

Fifteen minutes into our ride the skies opened up and we were treated to not one but two brutal bouts of hail and rain. I was determined that, despite the setback, this plan would somehow magically unfold.

We soldiered on until arriving at the halfway point of the trip, where we were greeted by a large opening in the trees with impeccable 360-degree views. We were absolutely drenched but somehow in wonderful spirits when Emily invited us to stop and take some photos. It was go time.

I pulled out my gear and setup the proposal video that I had shot, for her to watch on my iPad. She was quite confused when I handed her it to her but within a few seconds the tears and the rain started falling simultaneously. 

We were getting pelted with rain again but it didn’t matter. I got down on one knee, slipped the ring on her finger, and from under her helmet and yellow rain coat she quickly blurted out, ‘YES!’