Before the billionaires descended, Telluride was Colorado’s “Best-Kept-Secret.” The little town, nestled in a unique box canyon, was an unpretentious hang out for hippies and hardcore skiers. The rich movers and shakers looking for luxury with their skiing went to Aspen and Vail.
Telluride’s history as a rough-and-tumble Victorian mining town with rich deposits of gold and silver had attracted its share of reckless outlaws in the past, hoping to cash in on the wealth without doing the work. Butch Cassidy comes to mind. Supposedly, the first bank he ever robbed was the San Miguel Valley Bank – right there on Colorado Avenue – in 1889.
In the 1970s and 1980s Telluride became notorious for a different reputation – drugs and its legendary steep slopes offered a haven for hippies and free-spirited ski bums. Those slopes were not for wimps. The development of Telluride as a ski resort was in its infancy and the runs required more than skill – they required wild abandon with no fear. A massive 4,425-foot drop promised high adrenalin runs down cliff faces, all with breathtaking views of the surrounding 13,000 and 14,000 foot peaks of the San Juan Mountains.
It was uncrowded. It was dangerous. It was Bohemian. It was paradise.
Then Covid hit and the rich and super-rich fled to Telluride.
Telluride 2016 - Last glimpse before the deluge.
It was January. Time for an adventure!
My son was starting a new job on the East Coast and wanted to use his last vacation opportunity to improve his skiing while he was still in the West. Let’s face it – Vermont is cute, but the Rocky Mountains are awesome!
He chose Telluride.
“Do you want to come, Mama?”
Music to a mother’s ears.
A vacation in the gorgeous mountains of Colorado with my adult son? The very son who was soon to move four thousand miles away to New York City for a job that would keep him there for who knows how long. The son I might not have another adventure with for years.
I wouldn’t have missed this moment for the world.
He rented an Air-B&B house for a week.
Truly, the travel gods were smiling on me.
Yes. An entire house. Don’t be fooled. That was then. This is now. Today, in 2026, we couldn’t have afforded it.
Telluride immediately spoke to my love of history, small town charm, quirky people, and the thrill of majestic scenery. I mean, what could be more fun than a former silver mining camp at 8,750 ft. elevation that’s nestled in a box canyon with mountains rising all around it?
The perfect box canyon town. I’d never heard of a box canyon before.
I learned that glaciers formed this canyon during the Ice Age.
Before I went on this trip, I read one of the only two novels set in Telluride.
Telluride Smile is definitely in a Dashiell Hammett style, and the author, Raymond Ring, is good at channeling Hammett. He got a little over-the-top at the end with the government conspiracies and the really weird drug culture thing but, hey, that was part of the history of Telluride.
We’re talking very anti-establishment type skiing in Telluride. Even though the place makes a ton of money. Since the invasion of the billionaires and celebrities after Covid, it’s probably changed. And I’m sure it’s a lot more crowded than in 2016.
Speaking of the “drug image” for Telluride, it has a new face since the legalization of marijuana. Believe me, so many of the people I met, who lived and worked in Telluride, were spaced-out. It was almost comic. They were so laid back.
I don’t know if it’s still that way in 2026. Seems Telluride has become the Hamptons of the West. It’s all about real estate now. https://www.forbes.com/sites/rogersands/2025/06/19/the-uber-rich-are-flocking-to-this-small-mountain-town/
Uber rich or on-the-edge, it will always be about the skiing in Telluride. This is a ski runs map for 2016.
My son signed up with an instructor. This guy – Dave – talked the whole time they were skiing. Stories about the town and the people. One story was funny.
A friend of Dave’s had a girlfriend. One day she appeared wearing earmuffs.
(Why not? It’s really cold. When we were there, it fluctuated between 0 degrees and 34 degrees. That’s it.)
Anyway, her boyfriend’s response was, “Where’d you get those? Vail? People don’t wear earmuffs in Telluride!”
Supposedly she wore them for a while longer, but he mocked her so much she gave them up.
It was either the earmuffs or the boyfriend. Boyfriends are hard to come by in a small town like Telluride.
Laid-back hippy or not – there’s a real-world feeling to Telluride.
As one spaced-out guy at the ski shop told me, “Yeah. There’s still some of the old mining vibes going on here. It’s awesome.”
Actually, very little mining going on now, no matter what the sign says.
But it’s the intense skiing that sets the place apart. You can take a lift to 12,570 ft. and ski all the way down. Of course, my son did it. There are also areas where you can put your skis on your back and hike up to 13,000 ft. and ski down. He did that too.
Talk about oxygen!
Here’s a map of the high altitude runs back in 2017.
Check out that run from Palmyra Peak at 13,320 feet elevation!
They built a second housing area – Mountain Village – at 9,545 ft. elevation. This place is more upscale and “contrived” with many very expensive houses for sale. (Now, of course, the whole place is expensive.)
The Mountain Village area has more beginner slopes and there were lots of pint-sized skiers who were very cute.
So, here are my photos to tell the story of my time in Telluride.
First, a little bit of Telluride character and charm. “Hippy House” in town. What do you think?
Do they have a pot-belly stove? I hope so.
In case you ever wonder where you can go in an emergency. Here’s a ruined building with some very important signs.
Don’t worry. Everything’s cool in Telluride.
It was the end of December when we arrived. No one seemed eager to take down any Christmas decorations.
Like our neighbors across the street. I think they might leave the decorations up all year long. Christmas is slow in leaving Telluride.
There was an old guy (might have been one of the original Haight Ashbury transplants, definitely) who lived in the decorated house. He had an old dog (probably not an original Haight Ashbury transplant). Every morning the two of them would go for a walk around the block. Grumpy, both of them.
These are typical streets in town. I loved how charming they were. Old America nostalgia.
Reminded me of Calistoga in Napa Valley – without the snow of course.
The Elks Club is still operating.
Really!
Back in 1898, the local paper was the Telluride Times. Now it’s the Telluride Daily Planet. I wonder if that old clock is a time portal.
The New Sheridan Hotel was built in 1895. It’s still going strong. I suspect it’s been upgraded in the past 10 years.
The little snow bunny who kept coming around for a visit. Don’t even ask how many photos I took of him.
And everywhere – those incredibly beautiful mountains bringing breathtaking joy.
My son brought a drone and we had fun flying it around the clear mountain air.
Here it is descending to the mountain top. Not really, but a fun illusion.
I’m a tree lover from way back. Born and raised in Western Washington. I simply couldn’t get enough of the snow covered trees. Especially the contrast between the evergreens and the bare aspens. This was taken from the gondola up to Mountain Village.
Just one vista of the mountains from the gondola.
Mountain Village is just a gondola ride away. Next stop – 9,545 feet!
A Little Bit of Switzerland in Colorado
Step out of the gondola and you’re in a new world.
Mountain Village was so different from Telluride itself that I felt I’d slipped through a portal and travelled to Switzerland.
There was a sort of cuteness to the little town nestled at nearly 10,000 feet.
What better place to start a visit to Mountain Village than the Place des Crepes.
My recommendation is for the Nutella crepes. Mmmm!
Mountain Village is perfect for wandering around. Which I did as I wasn’t skiing those nerve wracking, insane slopes my son was tackling. I found so many fun things to do there to immerse yourself in the mountain vibe.
Like Ice skating. A popular little rink with children as I found out.
You can warm up by a cozy fire.
Or have a reviving drink outside even when it’s cold.
I loved the little fires burning at the tables.
Here are some more Swiss vibes for you.
Plus, there seemed to be more children enjoying the snow and practicing their skiing skills in Mountain Village.
And if you get bored you can always bungee jump.
No, that’s not a manikin. It’s a wild and crazy girl who simply got bored with skiing.
The gondola climbs even higher. Here I am at 10,555 feet. Top of the goldola.
Here’s my wonderful son on the outside deck at the restaurant.
We had a very welcome bowl of hot soup.
Another great adventure with my amazing son.
I have been so fortunate to have loads of great adventures in my life. Thousands of photos from my decades on this planet take me immediately back to wherever I want to go.
Like a nostalgic worm hole into the past.
Do you have adventures that hold a special place in your life? Moments that are like the brightest stars in a galaxy? Moments that rush back into your life without you consciously seeking them?
A name. An object. A particular smell in the air. A certain color of light through the trees. And, presto! You’re back there, wherever it was. Not just remembering but experiencing it all over again. Feeling it in a way that brings you such joy you want it to last forever.
My time in Telluride in 2016 was one of those adventures.