The Road Less Traveled: Part 1 — The many homes of calling Aspen ‘home’

My journey to call Aspen home has been anything but easy, a decade-long saga that’s instilled in me a deep appreciation for this town and its community. Every season, every move, every couch, every landlord. If you’ve lived here long enough, you know: Calling this place home means surviving a gauntlet of problems. And I am no exception. 

My Aspen origin story doesn’t even begin in Colorado. It begins in Cairns, Australia, where I was living out the tail end of a decade abroad. I had been bouncing through New Zealand and up the east coast of Oz — Queenstown, Gold Coast, Melbourne, Cairns — selling scuba dives and skydives over the Great Barrier Reef. My work-holiday visa was ending just as my sister was getting married. So I flew home.

I told myself I’d return to Australia, but the best laid plans of mice and men …

Back in Arizona, not wanting to let go of my travel lust, I found a job as a travel agent. Though it sounds kind of glamorous, it was actually working in a call center selling cruise and resort vacations from a cubicle. Fluorescent lights. No windows. No connection. No life. After a few months of existential erosion in the desert, I  found myself thinking about returning to the mountains. I’d worked winter seasons earlier in my life — Winter Park in Colorado, Sugar Bowl in Tahoe — and figured this idea wasn’t random; it was the mountains calling. This time, though, I wanted more than just snow. I wanted culture. Community. A nightlife. A town that felt alive after the mountain shut.

I considered Park City, Bozeman, Sun Valley. Then a friend, overhearing my list, cut in: “You want Aspen.” Aspen? I hadn’t even considered it. But they laid out the case, which included seeing live music at the Belly Up. It stuck. Where else can you ski all day then see the best live music at night?

Clearly, I was being summoned to Aspen! Within a week, I’d landed a job as a bellman at the Timbers Club in Snowmass. No housing, but I figured I could piece something together. So I booked a bunk at the hostel in Glenwood Springs and hit the road.

That hostel lasted two weeks. Daily blizzards and white-knuckled drives down Highway 82 weren’t sustainable. I turned to couch surfing and found a guy renting out his couch across from Buttermilk for $50 a night. Rough, but closer than Glenwood.

Eventually, a coworker came through with a tip about a short-term spot at Marolt. It was technically music student housing — like a college dorm — no kitchen, two rooms, a refrigerator, and a self-supplied George Foreman grill as my makeshift kitchen. My room was only accessible by walking through my roommate’s bedroom. At 32 and no stranger to roughing it, I grabbed it.

But Marolt was seasonal. When spring came, I had to move out again. I packed everything into my 1999 4Runner and left a deposit to return for winter. For the next six months, I traveled, then came back for another season.

This pattern repeated itself for years … Ullr Commons (a glorified dungeon with zero natural light) … a loft in a house I shared with a mom and her daughter (requiring me to tiptoe around after bedtime) … You get the idea.

By spring 2018, I had two goals: Save $3,000 for a security deposit plus first and last month’s rent and save for a wedding in L.A. The solution? I moved into the woods.

I camped all over, resettling every two weeks to dodge rangers. It wasn’t the romantic wilderness sabbatical I had imagined it to be. I showered at friends’ houses, worked long hours, and lived out of my truck most of the time. But I saved every penny and landed a spot on the Burlingame waitlist. Someone dropped out. I moved in. I now had a kitchen, my own bedroom, and heat. Progress.

But by season six, I was still bouncing: six addresses in six years, not counting the truck. Then came Castle Ridge — my first 12-month lease. I bought furniture, appliances, and decorations. Finally, I had long-term housing. 

Then the property owner declined to renew my lease. A nightmare, as I could no longer fit everything I owned in the back of my truck. 

I sold my stuff. Planning to move into my truck yet again, I lucked out — or so I thought — when a friend moved out of a basement in Snyder Park. I moved in and unknowingly rented from another horrible landlord. He would enter my unit unannounced, uninvited, and snoop around. Leaving weird notes like “don’t put food in the garbage disposal.” I decided to walk away from the nightmare housing. Again, I loaded up the truck.

As if answering my prayers for housing, a pop-up camper came up for sale. I bought it and parked it at what was then called the Intercept Lot, where the city had set up a shelter in place during the pandemic. I lived among men numbing themselves daily from both the harsh reality of life and the boredom of sheltering in place during a pandemic. Drinking hard liquor for breakfast, brushing their teeth with beer — those were my friends. For three months, that was home.

Then, finally, a break.

July 2020. APCHA called. Eleven people ahead of me failed to qualify for a Truscott unit. I was next. I had just enough in my bank account to cover the first and last month’s rent plus a deposit. I moved in immediately.

The first two years were brutal — working 60-hour weeks across three jobs, just to make rent. But I held the line. Year three came, and for the first time in almost a decade, I could breathe. I wasn’t worried about a surprise lease termination. I wasn’t living out of my car. I had a bed, a shower, and a door that locked.

Fast forward to today, I run my own business — Aspen Drone Company. I’m a certified drone pilot, merging storytelling with aerial cinematography. I also write and speak professionally. I’m self-employed. Self-sufficient. Stable.

I had done it. I had made Aspen home.

But to stay — to really make it here — you need more than grit. You need community. I had no money, no family here, and no backup plan. But I found something deeper: a local community that supported me through my lowest of lows and my highest highs (that’s a drone pilot joke).

That’s what makes this valley special. Not the mountains. Not the wealth. It’s the people.

They say you come for the winter but you stay for the summer.

Well I came for the winter, but I stayed for the community. 

And because of the community, I get to call Aspen home. 

Thanks for reading my stories and paying with your attention. Tune in next time to read about how I became a steward of Aspen.

Landon Hartstein is the founder of Aspen Drone Company, a media production company specializing in aerial cinematography. Combining his love to tell stories with his love for cameras. For media production services, contact him at Landon@AspenDroneCompany.com. To suggest a story ideas or just to say hi, contact him at LandonLikeAPlaneWrites@Gmail.com.