The Telluride gondola
The Telluride gondola
By Jason Diamond / November 11, 2019 8:58 am

It’s about seven in the morning as I sit outside of Baked in Telluride, picking at my croissant and drinking my coffee. There’s a black-billed magpie watching me. If I were back home in New York, it would be a pigeon, but in this part of Colorado, the bird that looks like a raven and a blue jay mixed together is pretty hard to avoid. I pull out my phone to look up some facts about the bird, and as I do, an older hippie that looks like he probably occupied various college administration buildings with Jeffrey Lebowski back in the day mutters something about how I should get off my phone and enjoy the morning before he pulls out a half-smoked joint, lights it up and walks away. 

I later find out the guy that I had a brief interaction with is worth somewhere around 10 million dollars because he got out of a startup you probably don’t remember right before the dot-com bubble blew up into a million pieces. That same day I also meet a guy who told me he grew up in Greenwich, CT, who got restless with the course his family name and wealth set him on so he sailed around the world until he ended up in Colorado; a former Facebook employee who “got out at the right time” — whatever that means; a German guy who used to be a race-car driver; an actor whose IMDB I had to look up but realized I was, in fact, familiar with; two people who mention they saw at least 50 Grateful Dead shows each; a poet, a handful of skiers and a guy who tells me he hasn’t had any reason to leave town in over a decade. 

All of this, I should mention, happens in the span of five hours. I’m told this is a normal afternoon in Telluride, Colorado. 

Main Street, Telluride

Growing up in the middle of the country, in a part of the Midwest that’s so flat we literally called a bluff overlooking a beach near my house “The Mountain,” we had to go far to ski. Most of us went up to Wisconsin or three hours west toward the border of Iowa. Not many families that I knew made the trek out to New England for reasons I could never quite ascertain; westward was the way to go. I always heard of trips to Sun Valley and places in California, but Colorado was really the place I associated with skiing. People talked up going to Vail or Aspen like they were visiting some holy land, and when I made my first visit to Aspen, before Dumb and Dumber and the chance to make jokes like “it’s the place where beer flows like wine,” it was as beautiful as I recall, but, damn, it felt fancy. And really, so did the families I knew who went out there — they were the ones whose kids would have filled the trope of the bad guy in a movie from the 1980s. 

And then there was another family I knew. One whose dad had an earring and drove a Porsche, and whose mom loved to mention she went to Woodstock. They were cool, and they went to this place called Telluride. 

The old mining town has always had some sort of reputation. Stories of its early days as a 19th-century mining town definitely earned it the “wild” label to go with its western location. But the prospectors eventually gave way to hippies and ski bums who thought they’d found some sort of utopia because, well, that’s what the place looks like, with mountains in every single direction.

It also feels little harder to get to than Colorado’s other ski havens. Vail is a little under two hours from Denver, Aspen three and change if you’re driving; both have small regional airports. Telluride, on the other hand, takes several hours to drive through, and only recently has become more accessible, with flights from all over coming in and out of Montrose Regional Airport, 65 miles away, and regional service from Telluride Regional Airport.

But the drive, especially the one on US-285 that takes you through two National Forests, is one of the greatest drives you can take in the U.S. Every moment of it is breathtaking, and once you make it to Telluride and hit Main Street, it feels as if you’ve really accomplished something big, and the view is your reward. The city is a treasure. 

But it’s no longer a well-hidden one.

Hence the millionaires and tech people. It isn’t under the radar, yet it still retains a sort of authenticity that a lot of places tend to lose once money starts rolling in. There’s no Whole Foods or Apple Store. People you meet tend to live there year round. It has that locals-first vibe that you don’t get in other well-known ski towns. The question is: Can it last? 

When you think back on the list of places that might have once been considered quirky and quaint, from parts of the Hamptons serving as a getaway for artists sick of Manhattan to the capital of Texas embracing the tagline “Keep Austin Weird,” and then you think of what they’ve become, how fast something can go from bohemian to bougie, there is reason to worry about Telluride. Sure, it’s tucked away, but it’s becoming more accessible by plane. For some places, that could signal a death knell — the end of Telluride.

Tom Watkinson, who serves as my guide around town and has lived there his entire life, thinks everything will be fine. You could say it’s part of his welcoming, jovial demeanor, but the guy who is a solid inch or two over six feet and has sideburns that he jokes earned him the nickname “Telvis” by some Russian visitors a few years earlier tells me that the push to keep housing for locals affordable will help his hometown retain some of its individuality. 

“It’s definitely a concern,” he says. “But the people that live here really care about it and want it to be the kind of place everybody can enjoy.” 

And that’s really the general attitude around town. A town, I should mention, that is relatively small — although it does open up once you hit the peak on the gondola ride to nearby Mountain Village, and you’re 10,540 in the air looking at the San Juan Mountains. Honestly, that part alone makes the trip to Telluride worth it.

Ultimately, a place is only as good as the people who live there. And whether it’s the people I talked to while making my way up the Imogene Pass, or the ones I listen to standing in line for the one and only place locals will actually stand in line for, Taco del Gnar, the people in Telluride are mostly good-natured ones. There’s a lot of North Face and Patagonia, but not a lot of the pretentiousness you might associate with an upscale mountain town as beautiful as Telluride. I don’t find myself thinking that it’s going to become the Key West of the West, some erstwhile rough-and-tumble town that trades on its funky past. 

There is the other part that stands out in my mind that makes Telluride a unique place when you stack it up against other places known for skiing: it’s way more than that. It’s biking. It’s snowmobiling. It’s hiking. And, as I jet down the backroads following MD, owner of Telluride Outfitters who supplies the Polaris RZR and talks up the lay of the land whenever we make a quick stop, I realize it’s just a general appreciation for the outdoors that means there’s really no such thing as an off-season in Telluride. That’s really what sets it apart. Yes, people who ski tend to fall on a certain side of the economic conversation, and when high season is at its highest I’m sure you’re going to find your share of undesirables who want to complain that their oat milk latte doesn’t have enough foam or that they can’t get a decent signal to upload their selfies on Instagram. But that’s par for the course just about anywhere these days. 

Maybe it’s the elevation, maybe it’s the legal weed or maybe it truly is the fact that people genuinely love the place and want to keep a certain vibe intact, but Telluride is one of the last truly enchanting places in America that hasn’t been overrun. Its cool hasn’t been scraped away, and just about everybody here has an interesting story to tell. Hopefully that never changes.