The Legendary Ski Friendship: Three Decades of Ripping Groomers

Some friendships are forged in classrooms, others on sports teams, but the rarest and most enduring are those shaped by shared passion on the mountains. This is the story of Mark, Tommy, and Kevin—three friends from Connecticut whose annual ski trips have transcended mere vacation to become the cornerstone of a lifelong bond.

The Beginning: Suburban Roots to Mountain Pursuits

In the quiet suburbs of Fairfield County, Connecticut, three ten-year-old boys met during a community youth sports program in the winter of 1995. Mark, the analytical one with an uncanny ability to plan the perfect route down any trail; Tommy, the natural athlete whose ski racing background would later shape their collective style; and Kevin, the adventurous spirit always pushing for “just one more run” even as the lifts were closing.

They first started skiing together during a school winter break trip to Stratton Mountain in Vermont, an experience that would forever change their lives.

“That first Vermont trip, we were just kids with rental skis and matching neon jackets from the local sporting goods store,” recalls Mark, now a senior portfolio manager at a prestigious Manhattan investment firm. “None of us could have predicted that thirty years later, we’d still be planning our lives around our annual ski week.”

The College Years: Keeping the Tradition Alive

When college threatened to separate them, they made a pact: no matter what, President’s Week would be sacred, reserved for their annual pilgrimage to the mountains.

During these formative years, each brought new friends into the fold temporarily, but the core trio remained constant. They upgraded from New England hills to Vermont mountains, pooling gas money for midnight drives to Killington in Tommy’s weathered Subaru Outback, cramming into budget motels where four often shared a room meant for two.

“There’s something about suffering together in a tiny motel room with broken heating that really cements a friendship. One year, we had to hang our soaking wet ski clothes from the shower curtain rod and sleep in our base layers. We woke up to frozen jeans.” — Kevin

The Professional Era: Evolution of Style

As their careers took off—Mark climbing the finance ladder, Tommy becoming a principal designer at Google, and Kevin building his successful business ventures—their ski trips evolved accordingly. The budget motels gave way to slope-side condos, and the gear upgraded from second-hand to top-of-the-line equipment.

Tommy’s background as a competitive ski racer became increasingly influential in their collective skiing style. His perfect carving technique, honed through years of gates and training, became the standard to which the others aspired.

“Tommy would film us and then break down our technique during dinner,” Mark explains. “He’d use salt shakers and utensils to demonstrate proper edge engagement. The waitstaff thought we were crazy, but those impromptu lessons transformed how we all ski.”

The Annual Pilgrimage: More Than Just Skiing

By 2010, the annual trip had expanded to a full week and established firm traditions:

Planning Night

Held each September at Mark’s Connecticut lakehouse, this evening of maps, weather data, and historical snow patterns has become almost as anticipated as the trip itself.

“Mark treats the planning like a financial prospectus,” Kevin jokes. “He has spreadsheets comparing snowfall data going back fifteen years, with weighted rankings for terrain variety, vertical drop, and even the quality of on-mountain dining.”

First Chair Ritual

No matter how late the previous night’s festivities, the trio adheres to their sacred “first chair” rule—they must be on the first lift every morning, without exception.

“The sound of that first chair departing the base, the creaking of the metal, the absolute silence of the mountain before anyone else has touched it—that’s as close to a religious experience as I get,” says Tommy.

The Annual Awards

Each final evening features a formal (but hilarious) awards ceremony, complete with hand-crafted trophies made from repurposed ski equipment:

Award Name	Description	Most Common Winner
Golden Edge	Best carving technique	Tommy (12 years running)
First Flight	Most impressive air	Kevin (despite numerous injuries)
Snow Ghost	First to disappear into powder	Mark (who once was lost for 2 hours)
Last Call	Final person to leave the bar	Rotates based on “life situations”

The Fischer Revolution of 2025

The upcoming 2025 trip marks a significant gear shift for the group. After years of skiing different brands, Tommy’s recent switch to Fischer Rangers has inspired a collective equipment upgrade.

“Tommy doesn’t make equipment recommendations lightly,” explains Mark. “When he sent us a group text simply saying, ‘Gentlemen, I’ve found the one,’ with a photo of his new Fischers, Kevin and I both booked demo days within 24 hours.”

The results were unanimous—all three will be carving on matching Fischer setups for the 2025 trip to Snowbasin, Utah.

“The versatility is what sold me,” Kevin explains. “These Rangers hold an edge on hardpack but still float in powder. It’s the perfect one-ski quiver for our annual trips where conditions can vary widely.”

Beyond the Core: The Extended Ripping Groomers Family

While the trio forms the foundation of the annual tradition, they’ve welcomed others into what they jokingly call the “Ripping Groomers Society.” Most affiliates are temporary—significant others who come for a year or two, college buddies who join for special anniversary trips—but only one person has earned permanent honorary member status: Joe.

“Joe is the only person we’ve ever unanimously voted into permanent membership, and he still hasn’t skied with us,” laughs Kevin. “But turning our inside joke about ‘ripping groomers’ into an actual website and lifestyle brand was such a dedication to the cause that we had no choice.”

Joe, who built the group’s website as a surprise gift for their 25th anniversary trip, transformed what began as a self-deprecating joke about their obsession with perfectly groomed trails into a platform celebrating their friendship.

“The website was supposed to be a small gesture,” Joe explains. “I had no idea they’d start using it to document every trip, complete with trail maps marked up with their favorite runs and detailed reports on snow conditions. What began as a joke has become a living archive of their friendship.”

Passing the Tradition to the Next Generation

Now in their mid-forties, the trio has begun including their children on alternating years, creating a new generation of “Ripping Groomers Junior Division.”

“Watching Tommy teach my daughter the same drills he taught me twenty years ago brings everything full circle,” says Kevin. “She now carves better than I do, which Tommy never lets me forget.”

The children range from ages eight to fourteen, creating a new dynamic among the families. What’s remarkable is how the children have formed their own bonds, mirroring their fathers’ friendship across generations.

The Legendary 30th Anniversary Trip

For 2025, marking thirty years since their first ski bus adventure, the group has planned their most ambitious trip yet—a two-week tour of the Alps, hitting iconic resorts across Switzerland, France, and Austria.

“We’re going back to our roots in some ways,” says Tommy. “We’ll be staying in some quirky alpine lodges rather than luxury hotels. The goal is to reconnect with what made us fall in love with skiing in the first place.”

The itinerary includes:

• Verbier, Switzerland - For its legendary off-piste terrain
• Chamonix, France - To attempt the iconic Vallée Blanche glacier run
• St. Anton, Austria - For both the challenging terrain and the après-ski culture

Mark has been planning this trip for over three years, coordinating with local guides, studying snow patterns, and even learning basic phrases in three languages.

The Legacy: More Than Just Turns

As they approach this milestone anniversary, the three friends reflect on what their ski tradition has meant beyond just the sport itself.

“My wife once asked why I couldn’t just ski with people in California where we live now,” says Tommy. “What she didn’t understand initially is that it’s never been just about the skiing. It’s about maintaining this thread through our lives, this constant that has weathered all of life’s changes.”

For Kevin, the tradition has been a grounding force: “In business, everything is always changing. Markets shift, technologies disrupt. But for one week every year, I know exactly who I’ll be with and what we’ll be doing. There’s profound comfort in that consistency.”

“The older I get, the more I realize how rare it is to maintain friendships across decades, distance, and life changes. Most people gradually lose touch with even their closest friends as careers and families take precedence. Our ski week has been the antidote to that drift.” — Mark

The Ripping Groomers Philosophy

What started as a self-deprecating joke about their preference for perfectly groomed corduroy over challenging powder or moguls has evolved into a life philosophy for the group.

“‘Ripping groomers’ has become our metaphor for finding joy in consistency and mastery rather than constantly chasing the extreme,” explains Kevin. “There’s something deeply satisfying about laying down perfect carving turns on a beautifully groomed run—it’s accessible, sustainable, and you can do it into your eighties if you stay fit.”

This philosophy extends beyond skiing into how they approach their careers, relationships, and health.

An Invitation to Create Your Own Traditions

As the trio prepares for their milestone 30th anniversary trip, they offer this advice to others:

“Find your passion, find your people, and create traditions that can weather life’s changes,” says Mark. “Whether it’s skiing, cycling, fishing, or cooking—the activity matters less than the commitment to showing up for each other year after year.”

Tommy adds: “And document it all. Our biggest regret is not having photos from those first ten years. Now we keep meticulous records, not out of vanity, but because we’re creating an archive of friendship that our kids will have forever.”

And Kevin’s advice? “Start now, whoever and wherever you are. Thirty years goes by in a flash.”

Are you inspired to start your own adventure tradition with friends? Have you maintained a similar friendship through a shared passion? Share your story in the comments below.

#friendship #traditions #group-trips #2025

Evolution of Careers, Equipment, and Bonds

As their careers evolved, so did their approach to skiing. Tommy, leveraging his design expertise at Google, became the group’s unofficial equipment consultant, meticulously researching the latest technology every season. Kevin’s business acumen resulted in strategic planning of their trips for maximum value and minimal crowds. Mark’s financial background meant they always had detailed spreadsheets tracking expenses and optimizing their budget.

“Tommy’s the reason we all ski as well as we do,” Kevin admits. “His background in racing pushed us all to improve rather than plateau. He’s got us doing drills on groomers when everyone else is searching for untouched powder.”

Tommy’s recent switch to Fischer Rangers has inspired a collective equipment upgrade. “When Tommy makes a gear change, we all pay attention,” Mark explains. “There’s usually a spreadsheet comparison that follows.”

“Our first chair tradition started in 2005,” Tommy explains. “We were staying at this slope-side condo at Killington, and Kevin bet us we couldn’t make first chair five days in a row. Not only did we do it, but we also made these ridiculous signs each day. The lift operators were taking photos by day three.”