The Road Less Traveled: Stop gatekeeping Aspen

Aspen is one of the most expensive towns on Earth. More than 100 billionaires own homes here. If you live here or have ever visited and seen the staggering beauty of this place, it doesn’t take long to understand why the world’s elite plant flags here. Between the pristine alpine backdrop and a town manicured like a five-star hotel, Aspen seduces almost anyone into fantasizing about living here.

But Aspen? Aspen is a heartbreaker. It teases you with dreamlike views and mountain-town charm and then slaps you across the face with a $25 salad and a $30 million real estate listing.

The cost of living is next-level. The town is surrounded by national forest, which means there’s a hard limit on building and expansion. Limited housing, combined with high demand, makes homeownership feel about as attainable as winning the lottery, while blindfolded, on a unicycle.

And though Aspen boasts the largest employee housing program in the country (over 3,000 units), the truth is that most people who dream of living here never will. The few who do either luck into employee housing, marry up, or work three jobs while living with four roommates and a cat that doesn’t belong to any of them.

Even sadder: Many locals born and raised here eventually get priced out of their own hometown. They move “downvalley” — to Basalt or Carbondale — in hopes of staying near their roots. But even those places are becoming unaffordable. The squeeze is real.

So yeah, Aspen gatekeeps itself. It doesn’t need help from the locals.

Which brings me to my point: If Aspen already has a 7,908 foot-level barrier to entry, why are so many locals acting like gatekeepers?

You know the ones. They scoff at tourists. Call people from downvalley “trash.” Engage in an ongoing local flex-off:

— “You’ve only lived here five years? That’s cute. It takes 10 to consider yourself a local.”

— “Oh, 10 years? Adorable.”

— “30 years? That’s nice, but were you born in Aspen?”

It’s a pissing contest in a snow globe.

And don’t even get them started on tourists. Many locals treat anyone who visits like they’re squatters. “They’re taking up space. They’re driving up prices. They’re ruining Aspen!”

Sound familiar?

Let’s be real: This behavior is shameful. Tourists aren’t the enemy. And neither are the electricians commuting from Rifle or the ski instructors coming from oceans away. They’re the ones keeping this town functioning, building your houses, pouring your drinks, running the lifts. 

Aspen locals: You don’t need to gatekeep Aspen. Aspen already does that just fine on its own.

The town is expensive, exclusive, and logistically ridiculous. No one’s sneaking in under the radar. No one’s storming the gates. If there’s any purity left to preserve, it’s already long gone. The secret is out — and has been for, oh, I don’t know, 40 years.

Can’t find parking at North Star anymore? Yeah, neither can anyone else. Horrified at your $300 dinner for two? Yep. Join the club. Frustrated that every campsite within 40 miles is full? Welcome to the party. These are not new problems.

So instead of chasing some fantasy version of Aspen that existed in the ’70s, maybe try something radical: Be kind.

I’ve traveled all over — Thailand, Central America, Australia — and the common thread in tourist towns that thrive is this: hospitality. In Thailand, they greet you at the dock with menus and smiles. In Costa Rica, locals embody “pura vida” — pure life. In Hawaii, it’s “aloha.” These aren’t flippant sayings. They’re mindsets. Ways of living. Ways of including people.

Yes, Aspen isn’t exactly desperate for tourist dollars. But the locals? They are. The waiters, bartenders, real estate agents, guides, ski techs — they rely on tourism. So why treat tourists like a nuisance?

Try being helpful. See someone walking in circles on Hyman with Google Maps open? Ask where they’re headed. When someone complains about how expensive food is, nod in solidarity and then suggest a hidden gem — Big Wrap, New York Pizza, Zane’s. These aren’t secrets. They’re lifelines.

You want to protect Aspen? Great. Do it by showing it off. Be a steward of this place, not a gatekeeper. You don’t need to play sheriff of Malibu in “The Big Lebowski” throwing coffee mugs and screaming “get out of my town Lebowski, stay out of Malibu dead beat.”

This town is magical. And if you’re lucky enough to live here, your job, nay — your duty — is to help people experience that magic. Just like people did for me in the places I’ve traveled. I’ve been the lost tourist. I’ve been the guy who couldn’t figure out which bus to take. And I’ll never forget the locals who helped, smiled, and made me feel welcome.

Aspen needs more of that. More stewards. Fewer guards at the gate.

Look, I get the impulse. You love this place. You’re scared it’s slipping away. But you’re not going to save Aspen by sneering at a family in rental ski gear trying to find Paradise Bakery. You save Aspen by being kind, patient, and generous. That’s the version of this town worth preserving. Mind. Body. Spirit. 

So next time you feel the urge to groan about tourists or flex your “local” status, stop. Choose generosity over judgment. Choose “aloha.” Choose “pura vida.” Choose to be the kind of Aspenite who welcomes the world in — because let’s be honest, most of them won’t make it past the front door anyway.

Let’s stop gatekeeping Aspen and start sharing it to those fortunate enough to experience the magic here. Leave people wanting to come back even though the barrier to entry is so high they likely never will. Make guests, visitors, tourists, and strangers long to return to this incredible place instead of taking with them memories about how expensive, entitled, and superior Aspen can be. There’s enough to go around.

Just a humble local’s opinion that I’m sure I’m wrong about. But Aspen could use a few more locals who care about the guests visiting their home and a few less gatekeepers protecting a place that’s already very well protected. 

Thanks for reading my stories and paying with your attention. Tune in next time for the final part of this series.