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 makes for the ultimate backdrop to propose to your better half in nature's unrivaled magic. 

It was about time.

My girlfriend Jessica is compassionate and kind. She’s smart and goofy and loves to travel. And is very patient. It had been four years of growing together and we found ourselves at a point where we both knew it was about time for me to put a ring on it. I found the conflict free stone that I knew she’d love and had dreamt up a myriad of original ideas of the magical ways to pop the question. Now, the final part of the puzzle was when and where to do it.

I put out the feelers to friends and family and the feedback was great. A rooftop in Downtown LA. The beach. A hike in a national park. New York. Aspen. Paris. Wait, Aspen? In the summertime?

For me, the mere whisper of the word Aspen invoked images of billionaires frolicking on powder covered mountains, aprés ski with magnums of Dom Perignon and Harry and Lloyd scrambling to return a briefcase to its rightful owner. So how would we fit into this world? We love to be outdoors, are always game to travel and do cool stuff together, so why not give this place a shot? Plus, I was pretty confident that the air quality was a bit nicer than LA.

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.

48-Hours To Go: Roof Over Our Head

We arrived in Aspen on Friday afternoon and within 30 minutes of landing at the local airport we found ourselves checking into the charming and conveniently located Molly Gibson Lodge, also a 'Kind Hotel' on Kind Traveler. Charlie greeted us at the entrance and welcomed us like we were long lost friends. He lead us past the heated pool and jacuzzis (yes please!) to our Molly King Room. With its wood burning fireplace and paneled walls it seemed to jump right out of a 70's era alpine film. I could see the smile growing on her face and realized that we had definitely made the right decision to come here.

Pro-Tip: Molly Gibson Lodge offers exclusive rates on Kind Traveler when you give a $10 nightly donation to Aspen Hope Center, helping to provide mental health education and services to those in need in the local Aspen community. 

43-Hours To Go: Food In Our Bellies

My nerves began to get the better of me and I realized that we had to get some food in us. We found our way to Clark’s Aspen, a bright and airy recent Austin transplant that certainly lived up to the hype. While the restaurant was bustling with smiling patrons, the Bar Gods shined down on us as two seats appeared upon our arrival. We ponied up to the bar and our delightful bartender/concierge/tour guide, Lacie, took us on a journey of the menu and gave us a detailed account of how their Texas gem ended up in this Colorado ski town. 

The food was on-point but we were especially pleasantly surprised by the sophistication of the grilled Tuscan kale with toasted pine nuts and the grilled brussels sprouts, both char-grilled to perfection over a wood fire. Delicious. We sealed the deal for our taste buds with the salted butterscotch pot de crème and macadamia lace cookies.

Thankfully the food did a great job bringing my heart rate to a steady pace for the moment, and I’m sure the wine didn’t hurt either. As our meal was winding down it dawned on me that I’d be getting down on my knee in less than two days. Dinner was a complete success. Now, it was time to get some sleep.

31-Hours To Go: Opt Outside

We kick-started our day with complimentary eats and caffeine from Molly Gibson Lodge and then hopped on a shuttle to Glenwood Springs for a half-day of rafting the Shoshone Rapids with Blazing Adventures. Aspen in the summer has a host of offerings for outdoor adventurers, and is particularly known for its white water rafting. What better way to spend an afternoon then to scare my partner out of her mind and try something she had never experienced?

The knowledgeable and fun-loving guides put my soon-to-be-fiancé’s nerves to rest and she ended up tackling the Class III whitewater like a pro. Our journey together down the river not only got the adrenaline flowing and offered ridiculously gorgeous views of the red rock formations and lush vegetation, but it also solidified how well we worked together in moments of adversity and fear. 

Things were working just as I had planned. The day wouldn’t have been complete without the riverside barbecue organized by the Blazing Adventures staff. Flavorful veggie burgers, homemade coleslaw and chocolate chip cookies made the drying out process much easier.

24-Hours To Go: Explore

It was officially 24-hours until I would pop the question and I was struggling to keep it together. I seriously needed to keep busy and breathe in as much of the fresh mountain air as possible. We hopped on the complimentary bikes from Molly Gibson Lodge and spent the remainder of the afternoon exploring the Aspen Saturday Farmer's Market at the base of Aspen Mountain.

Aspen locals grabbed their fresh veggies for the week while tourists from around the world perused and sampled the Colorado-made, grown and produced items. My girlfriend’s favorite local company was Aspen Kettle Corn. She loved how their popcorn was a little sweet, a little salty, and popped with love. Oh, and the fact that the portions were enormous didn’t hurt, either.

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!’

"That wonderful moment in Aspen provided us with a life lesson that we weren’t expecting, and it turned out to be quite the metaphor for marriage."

We may have the best intentions when starting out a life together but the sunny days will no doubt be interrupted with storms. What really matters is how a couple weathers these storms together and how it can make them stronger. Aspen, you threw some curve balls into my plan, but truthfully, I wouldn’t want it any other way. 

It was the perfect backdrop for the beginning of this new chapter in our relationship. 

Jeff Berg is a Canadian born & New York bred, Los Angeles based actor & traveler. He is known for his work on Battlefield 1 (2016), Mirror's Edge: Catalyst (2016) and Love, Death & Robots (2019).