Oprah's favorite ski town is a hidden gem.
Telluride

Tucked away in the Southwest Colorado San Juan Mountain Range sits Telluride. Nestled among the soaring peaks of the Rockies, you’d be forgiven for believing you’d stumbled into Switzerland.

A bizarre history of bandits, miners, and hippies has fused over the last century and a half to produce one of the US’ coolest little towns, where ski slopes are complimented by indie art shows and some of the best music festivals in the country. Unlike so many of the glitzier resort towns, Telluride has clung to its Victorian charm, rejecting the mainstream to the point that no franchise restaurants or stores grace its streets. Independence runs through the town’s veins.

And sure, Oprah likes it enough to have a house there. But don’t take her word for it.

Instead, we want to let you experience this hidden mountain gem for yourself by sending you on an epic 3-day Ski Getaway — along with $500 to spend for travel. 

So grab that ski gear out of storage and enter to win here!

In the meantime, welcome to Telluride.

5 things you can’t miss in Telluride

Take in a festival

festival crowd at sunset outdoors

Telluride has become one of the country’s best towns for festivals. The festivities are year-round, drawing hobbyists, music fans, film nuts, and a menagerie of other interests on different weekends to indulge in their passions.

One of the most famous is the Telluride Bluegrass Festival. The celebration of music has been running for fifty years and draws some of the biggest names in the genre. If country isn’t your thing, hang on till July, and you can enjoy Ride Festival, a rock-heavy lineup that has featured Pearl Jam and Widespread Panic in the past.

Food and drink festivals make up a good chunk of the calendar, of course, with the Telluride Wine Festival being a particular highlight. The mushroom festival is technically a food festival, too…although it swings more towards the psychedelically inclined than anything else.

On top of all these, the Telluride comedy and film festivals are permanent fixtures. The jazz festival, the Autumn Classic car show, the Telluride Horror Festival, the Fire Festival, and the Plein Air Festival help make up the numbers. So as far as non-skiing activities go, you’re truly spoilt for choice.

Hit the slopes (duh!)

skier on mountain

Whatever your reason for visiting Telluride, it’d be a shame not to hit the slopes at least once on your trip. Some of the best skiing in the country is found within a stone’s throw of the town, and thanks to its location, you’ll rarely be jostling with the crowds as you do in other resort towns like Aspen.

The region has over two thousand acres of skiable terrain, so whether you’re a seasoned pro or slapping the skis on for the first time, you’re covered.

Beginners can enjoy the Sunshine, Ute Park, and the Prospect Bowl, which are all phenomenal wide open slopes to learn the basics. There’s even an unintimidating four-mile trail that leads from a stunning peak all the way down to the village to ensure that even though you’re only getting started, you’re still getting to take in the best of the scenery.

At the other end of the spectrum, The Plunge is the ultimate adrenaline rush. It’s a black diamond run that plunges almost 3000 feet into the town of Telluride, offering some of the best views of the entire valley. Just under half of the available slopes are designated for advanced or expert skiers.

Get adventurous

Telluride is in the heart of some of the most stunning scenery in the world. To visit and not get out to explore the area’s breathtaking nature would be a travesty. Fortunately, there are a variety of ways to do so.

For avid hikers, there are a number of amazing trails to get stuck into. Bear Creek and Bridal Veil Falls trails are two of the most popular, allowing hikers access to some astonishing natural landmarks like cascading waterfalls, awe-inspiring geo-formations, and unparalleled vistas.

For those hoping to get even more hands-on, canyoning trails, rafting experiences, and rock climbing opportunities are abundant in the area. Activities like these are the reason many locals hung around in the seventies and sixties, so go on and ask a local for the best spots to do each one. 

Gaze out from the gondolas

telluride gondola

If you’re less into the adventure part of adventuring or simply want to enjoy the view without interruption, how about sitting down with a splendid view?

The Telluride Gondola is arguably the best way to take in the spectacular scenery, all without moving a muscle. Enjoy the breathtaking views in all their glory for about 13 minutes. 

We don’t recommend it to people afraid of heights, as it does dangle at 10,500 feet. We do, however, recommend catching the gondola during sunrise or sunset. It runs from 630am to midnight in the summer and winter.

Take a stroll down Main Street

main street telluride

Once you’ve had your fill of the slopes, trade the snow for a stroll down Main Street, also technically known as Colorado Ave. 

The old Victorian style architecture and brick lain building will transport you back in time to the Butch Cassidy days. You can actually see the site of his first bank robbery if you go to the Appaloosa Trading Company. There are many more historical sites to take in and you might consider stopping by the Telluride Historical Museum and snagging one of their historical walking guides so you can see them all. 

One place you can’t miss is seeing is the historic and intimate Sheridan Opera House is putting on a show while you’re there. I’m sure any show is great but the interior of the theater is a feast for the eyes on its own as well.

Of course, the history is nice to take in but Main Street has truly been transformed. You could spend an entire day exploring all the quaint boutiques and scrumptious restaurant menus.

A few stand outs include La Marmotte for a more upscale and exquisite French dining experience and Smuggler-Union Brewery for more of a pub experience. 

Want to uncover the best of Telluride?

Check out Next Stop: Telluride for the best places to stay, eat, and explore in Telluride!

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