To take us through Telluride, we have Scott Caputo, a New York native who has been a fixture on the Telluride scene for 15 years.
Scott, his family and his entourage epitomize the educated, beautiful and well-traveled crowd you would expect to see in this gorgeous ski town. We scratched this surface though with Scott and found a heart of gold, as well as what we knew before; there is never a dull moment with Scotty Caputo. Scott lives Telluride like a Local, and with his recommendations in this down-to-earth ski destination of the elite, you can too.
Three words Scott uses to describe Telluride: Stunning, Entertaining, Eclectic.
Three words we use to describe Scott: Gregarious, Daring and all-around Cool.
Galavante: Tell us a bit about yourself.
Scott: I was born in NYC and moved to Greenwich when I was 8 years old. I lived there until I went to UVA for college. Post-college, I had a two-year stint in Chicago but returned home to New York City.
Galavante: What brought you back to New York?
Scott: Besides my family and friends, I went to work in Finance. Eventually though, I had the opportunity to start my own company, Sir Drake.
Galavante: Sir Drake sounds quite regal.
Scott: It was a great experience. Sir Drake was a high-end men’s sportswear boutique clothing company. We specialized in polo shirts, and were in about 50 stores worldwide, including Blue & Cream in New York. We eventually wound down the company as my partners and I decided to pursue other opportunities. I’m now at Darden Business School in my second year. Sir Drake taught me everything though about running a business.
Galavante: How long have you been going out to Telluride?
Scott: I have been going to Telluride since 1996. My family and I started staying at the Peaks Resort. We fell in love with Telluride and eventually bought a house in the Mountain Village in 2001.
Galavante: How often do you go out to Telluride?
Scott: I try and go 2 to 3 times a year. It’s one of my favorite destinations in the world.
Galavante: What makes Telluride unique from other ski resorts to you?
Scott: Telluride can be challenging to get to, but it’s actually a blessing. It keeps the ski lines down and you never have to wait more than 10 minutes to get on the chair lift. It also keeps it less commercial than other ski resorts in Colorado.
For skiing, I love that Telluride has a huge variety of challenging slopes, which are continually being expanded. You’re always skiing new trails, and you’re never bored. I don’t think there’s a place in Colorado that is situated in between more breathtaking mountains and cliffs. The panoramic views are stunning.
Galavante: What is skiing like for beginners?
Scott: If you can get a lesson with Telluride Ski School – do it. Everyone is fun and knowledgeable. They will make you a better skier and you will enjoy your experience. My family and I have been skiing with our friend Freddy for years. He’s like the Mayor of Telluride; he knows everyone.
Galavante: What’s the best time to go to Telluride?
Scott: I can’t decide on the best time. While Telluride is known for the snow, there is actually more activities to do in the summertime including fly fishing and hiking, plus all the incredible festivals that Telluride hosts. In the spring, the skiing is probably best – it’s warm and there is a huge basal of snow, but Telluride does an outstanding job during the holiday season. This past year, we brought 26 friends and family to our home to celebrate Christmas and the New Year. It’s beautiful during Christmas time.
Galavante: What are your top restaurants?
Scott: In the Mountain Village, I would recommend La Piazza, where they treat you like family. The food is outstanding and the service is impeccable. My family and I have been going there for years and are consistently blown away. In Telluride, I would also recommend Rustico’s, also for fine Italian food. The pasta is as good as anything I can get back in New York.
My favorite, though it’s stiff competition, is the Sheridan Chop House for it’s glowing atmosphere with happy people. The food is incredible; they serve the best elk I’ve ever had. I always try and go there at least once when I’m in town.
Galavante: What are your top bars?
Scott: The Sheridan always seems to be the main attraction. Great mix of locals and visitors. You can play pool in the back or you can mingle in the front room. O’Bannon’s is one of my favorite dive bars. It is mostly locals. The place is run-down, but in a way that it adds so much character. A mixed drink is more like liquor and a splash of something else. Always a great time.
Galavante: Any other insider spots?
Scott: For BBQ and incredible ribs – go to Fat Alleys! I always make it a point to stop in town for lunch during the ski day to catch up with friends and family on the trip. Fat Alleys is one of our favorites. They have something called a Mitch Morgan – which is a bourbon shot-usually George Dickel whiskey-chased with a piece of bacon.
