A Guide to Telluride


When you think of a guys-only skiing and snowboarding trip, it’s natural to assume that a bunch of friends traveling without their wives or girlfriends will “go big”: long days on the mountain, afternoons full of cold beers and bourbons, and nightly Texas Hold ‘Em tournaments. But there’s also a lot of couch time, long soaks in the hot tub, and great storytelling.

BACK left to right: Michael Stern, Robert Cooper, Hans Maestre, Michael Wendrow, Mark Hirsch, Neal Sklar, Greg Levine, Howard Weinberg, Moshe Cohen and Frank Cirisano. FRONT left to right: Brian Foster, David Bloom and Rich Paz.

For all that and more, Telluride, Colorado, was the perfect destination for our annual 5 Guys and a Mountain trip this past winter. Even better, we somehow assembled the coolest, craziest group of 12 guys ever in our eighth year of arranging these trips. We had a couple lawyers—one known for his legendary love of super smooth “corduroy” snow, the other a laid-back daredevil who loves double-black runs—a real estate developer who brought his own drone to the mountain, and his friend, an entrepreneur in the food industry who kept us all laughing (especially when he split his ski pants open attempting an expert ski run). The city of Aventura was well represented, with a veteran police officer, a first-time skier (and master at group selfies), plus a commissioner and two of this magazine’s publishers, both expert skiers. We had a chiropractor, a local surgeon and super-fast skier who made it back for his record eighth adventure with us, and an entrepreneur from Golden Beach, who learned how to ski after realizing that skiing doesn’t hurt as much as snowboarding. The real estate investor who made his first 5 Guys trip has already committed to next year’s trip. And then there’s me, with my 25 years of black diamond snowboarding skills.

Beautiful (without trying too hard)
For most of us, this was our first time in Telluride, and it was a solid choice, as we discovered almost immediately that the town has a vibe all its own. We definitely love the endless terrain of Vail, the mining town history of Breckenridge and the glitz of Aspen. But Telluride is something else altogether.

After flying into the regional Montrose Airport late Friday, we took a shuttle to our condos, which were located downtown and within walking distance to bars and restaurants. For our first night, we arranged dinner at West End Bistro, located inside the Hotel Telluride just two blocks from our condo. The staff of this small, chic hotel set us up at a long table near their giant fireplace; it was the perfect spot to unwind, while our self-appointed spiritual leader led us in an informal Shabbat service.

Our first day on the mountain couldn’t have been easier. If you’ve been to the mountains, you know it’s all about convenience. We took a quick walk across the street to the gondola to take us up the mountain. The lines were minimal and there was none of the chaos or hustle you normally find at the bigger Colorado resorts. Telluride’s long runs feature plenty of spots for tree skiing, and too many options for après ski drinks around a fire pit. This year’s trip coincided with the Super Bowl, so on Sunday we quit a little early, gathered everyone in a condo and ordered Chinese food delivery.

The Telluride Mountain Village, newer and more like what you expect from a resort, is separate from downtown and accessible via a short gondola ride or a quick drive, and that’s a good thing. We could have stayed in this area, but we preferred to be closer to downtown. That’s because Telluride is a real town that the locals love. It’s squeezed into a box canyon, surrounded by the highest concentration of 13,000- and 14,000-foot peaks in the United States. There aren’t that many stoplights. There are fewer t-shirt shops. The town is beautiful without trying too hard.

After two other 5 Guys trips to Aspen and Vail, our Golden Beach entrepreneur came to Telluride with the goal of switching from snowboarding to skiing. After just one day of lessons, he made the blue runs look easy. “Skiing that blue run with the boys was definitely a highlight,” he remarked. “But sweeping the Super Bowl lottery may have been better.”

Our group really tapped into something special this year. Maybe it was doing shots in the Last Dollar Saloon with a few locals on a Monday night, all of whom were anxious to listen to our wild crew tell their crazy stories, or maybe it was the Telluride terrain covered in fresh powder, with plenty of opportunities for our guys to get lost while skiing through the trees. In any case, it all added up to a unique and memorable experience for everyone.

Lasting memories and new friendships
Throughout our four-day, five-night adventure, I was reminded of the guys’ trips that my father used to take with his friends when I was a kid. He would spend days, weekends, and sometimes entire weeks on the boat scuba diving and spearfishing in the Bahamas. There was always a Heineken or two at lunch, and they would pass a bottle of ouzo around the table at night while dining on the fish and lobster they’d caught earlier in the day. They made lasting memories, and friendships that continue to remain important even today.

Now that we’re all a bit older, I see the wisdom. A few days on the mountain with your buddies is the perfect antidote to daily life. That kind of camaraderie has no price tag and doesn’t require an agenda. You can mix up the days with snowmobiling and snowshoeing, or you can go hardcore and hit the mountain at 8:45 am, heading back to the bottom only when ski patrol insists you leave (that’s us).

“That camaraderie was a huge highlight for me,” said our 22-year veteran of the Aventura Police Force, who took his first 5 Guys trip this year and enrolled in ski school for the first time. “I was the new guy. I expected people to be standoff-ish, but it was completely the opposite—it felt like being amongst family.” He loved taking ski lessons and was blown away by the mountains and the alpine environment.

I’m a snowboarder who often hangs out with skiers. And we’re not all at the same level. We’ve got both experts and beginners in our group. The point is, you shouldn’t let varying skill levels or interests keep you from having a great guys’ trip. The beginners might spend a half-day in lessons, while the experts torture themselves on the bumpy black diamond runs. Meet up for lunch mid-mountain, and then beers at the base as the sun is setting. Doesn’t that sound like a perfect day?

Some of our favorite spots in Telluride:

Last Dollar Saloon. Originally built in 1899, the distinctive brick building on the corner of Colorado Avenue and Pine Street has been a clothing store, a garage, a stained glass factory and a pizza restaurant, but the last 40 years it’s been serving drinks as one of the coolest ski town bars we’ve ever visited.

Black Iron Kitchen & Bar. Located in the Mountain Village, this is a great spot for après ski, with outdoor fire pits, live music and handcrafted cocktails in abundance. If you’re up for a challenge, grab some friends and order their 96-oz. Madeline Mule featuring Telluride vodka, lime, ginger beer and mint.

Smuggler’s Brew Pub. Located just a few blocks from the base of the free gondola in town and filled to the brim with locals and tourists, this joint is tons of fun and has a huge beer menu. Food is pub grub, featuring burgers, salads and pastas done right.

Oak Beer, Bourbon and BBQ. Located at the base of the Free Gondola, it’s a great spot to have a few beers after a day on the mountain. Try their famous fried okra.

Alpine Wellness. Tucked upstairs behind a gourmet hamburger spot in the middle of downtown, Alpine Wellness is the longest running locally owned dispensary in Telluride, selling 100 percent soil-grown cannabis, and they make their own edibles and infusions.

Telluride Facts:
• It was founded in 1878 as Columbia, Colorado, and forced to change to Telluride in 1887 due to Post Office confusion
• Butch Cassidy robbed his first bank here in 1889
• The ski resort opened in 1972 with 5 lifts
• There are 2,000+ skiable acres
• Of 148 trails, 23 percent are beginner, 36 percent are intermediate, and 41percent are advanced/expert
• There are 19 total lifts
• Maximum elevation is 13,150 feet
• The Galloping Goose run is the area’s longest at 4.6 miles

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