Stories

As we sit less than a month away from Hipster 2026, the excitement is already building. This year marks something truly special: the 10th year reunion of Hipster — ten years of hikes, pond swims, bonfires, laughter, family, friends, grit, babies, toddlers, dogs, golf, side-by-sides, questionable outfits, great food, and unforgettable memories in Jay, Vermont.

And before the weekend has even arrived, Hipster 2026 is already off to an incredible start.

The next generation continues to grow with three new Hipster babies entering the world in the first half of 2026: Annie, Sloane, and Morgan. Their arrival is another powerful reminder that Hipster is not just a tradition we remember — it is a tradition being handed down. The next generation is being welcomed, raised, and properly cultured in all things Hipster: mountain air, pond life, family chaos, Vermont grit, and the sacred art of showing up.

Hipster 2026 will also celebrate a major milestone for Footie, the ceremonial patriarch of Hipster, as he enters his 90th year. Footie has always represented the spirit of joy, loyalty, humor, and presence that makes Hipster what it is. To have him part of this 10th year reunion gives the whole weekend even deeper meaning.

And the family celebrations keep growing. JT and Gabby are planning a December 2026 wedding, adding another joyful milestone to a year already filled with babies, legacy, reunion, and new beginnings. Their upcoming wedding is one more reminder that the Hipster story keeps expanding — through marriages, births, friendships, family ties, and the shared traditions that bring everyone back together.

There will be more to come in the full 2026 recap, but already this year feels different. Bigger. Deeper. More generational.

The babies are arriving.

The family is growing.

Footie is entering his 90th year.

JT and Gabby are preparing for their wedding.

The mountain is waiting.

The fires are ready.

The stories are still being written.

Ten years in, the Hipster tradition is not slowing down.

It is alive.

It is growing.

And the next generation is already learning the way.

After the road-trip adventure of Hipster Colorado in 2024, Hipster 2025 came home to Jay, Vermont — back to the mountain, the pond, the pool, the bonfires, the food, the laughter, and the place where the tradition first found its footing.

And this year, the next generation set the tone early.

Brendan Michael Cotter II and Hunter Osgood brought the energy right from the start, playing splash in the pool and reminding everyone that Hipster is no longer just carried by the original crew — it is being handed down, laugh by laugh, frog by frog, ride by ride.

ZuZu — Suzanne — taught Hunter how to catch frogs, officially continuing one of the great pond traditions of Hipster weekend. And Brendan had his first ride on the four-wheeler, another milestone moment in the growing story of future Hipsters learning the ways of Jay.

The next generation kept growing, too. After welcoming Jane Semple and Viv McGovern in 2023, the Hipster squad welcomed Ellie Semple in 2025, adding another name to the future roster of hikers, pond swimmers, frog catchers, and bonfire regulars.

Hipster 2025 also saw the start of what may become another great tradition: the Jay Peak Golf Squad. The weekend kicked off with MPM and Sue hitting the links on Friday before Hipster, joined by the squad of guys and setting the stage for golf to become part of the growing Hipster rhythm.

But the heart of Hipster 2025 was captured in this year's T-shirt design.

The shirt reflected the challenge, grit, perseverance, and total class of Alexa McGovern as she continued her recovery from breast cancer. The Alexa slogan read loud and hit the heart:

Optimized! Resilient! Unapologetically Alive!

Alexa embodies so many of the qualities that Hipster has come to stand for: grace under pressure, strength without self-pity, humor through difficulty, and the courage to keep showing up fully alive. Her journey gave Hipster 2025 a deeper meaning and reminded everyone that resilience is not just a word — it is lived.

Of course, Libby and Bailey arrived on scene for yet another Hipster, bringing more friendship, more energy, and more proof that once people become part of the Hipster story, they keep finding their way back.

There was pond time. There was pool time. There were bonfires. There was great food. There were even better friends. And there were memories that will live long after the weekend ended.

Hipster 2025 was a return to Jay, but it was also a reminder that the tradition is still growing. The babies are becoming toddlers. The toddlers are becoming frog catchers. The golf squad is forming. The mountain is still calling. The fires are still burning.

And the Hipster spirit remains exactly what it has always been:

Family. Friends. Movement. Grit. Laughter. Love. And showing up — year after year.

On to Hipster 2026.

Hipster 2024 was both a celebration and a pivot.

The biggest celebration of all came in June of 2024, when Brendan Michael Cotter II — BMCII — was born, officially bringing a new generation into the Cotter family and into the wider Hipster story. A new Brendan had arrived, and with him came another reminder that Hipster has never just been about a hike. It has always been about family, legacy, movement, friendship, and the stories that keep growing year after year.

By this point, the Hipster next generation was clearly taking shape. Jane Semple and Viv McGovern had joined the Hipster story in 2023, and now, in 2024, BMCII added another name to the growing crew of future hikers, pond swimmers, frog catchers, side-by-side riders, and bonfire regulars.

And in 2024, Hipster did something it had never done before.

Hipster took to the road.

For the first time, the tradition left Jay, Vermont, and headed west for the inaugural Hipster Colorado. The Osgoods, the Cotters, and a whole new crew of Colorado friends gathered in Golden, Colorado, to bring the Hipster spirit to the mountains of the West.

The crew included Liam, Dillon, RJ, Thomas, Natalie, Brendan Michael Cotter II, Brendan, Sue, Suzanne, the Osgoods, and new Colorado friends like Rachel and Clayton, who joined the adventure and helped make the first Colorado edition feel like it had always belonged.

Instead of Jay Peak, the crew took on Lookout Mountain in Golden, Colorado, climbing into a different kind of mountain test. At roughly 7,300 feet, this was a bigger elevation challenge than Jay Peak’s 4,000-foot climb. The air was thinner, the views were wider, and the Hipster tradition proved it could travel, adapt, and still feel like home.

Hipster 2024 was also a year of love and new beginnings. Matt and Emily got engaged, with their wedding planned for September 2024 back in Vermont — another reason the year felt like a bridge between generations, families, and places.

Colorado was awesome. It was big, beautiful, expansive, and full of energy. It showed that Hipster is not limited to one mountain, one trail, or one state. The spirit can travel wherever the people gather, wherever the laughter starts, and wherever someone says, “Let’s hike.”

But as great as Colorado was, there was still one truth everyone knew:

It was time for 2025 to come home.

Back to Jay. Back to Vermont. Back to the pond, the bonfires, the mountain, the memories, and the place where it all began.

Hipster Colorado proved the tradition could grow. Hipster 2025 would bring it back to its roots — and welcome another new member of the next generation, Ellie Semple, into the Hipster story.

Hipster 2023 brought a lot of changes, a lot of laughs, and a whole new generation stepping into the tradition. It was a year full of firsts, surprises, pond swims, good food, bonfires, and the kind of family energy that keeps the Hipster fires alive.

The theme for Hipster 2023 was the “Top 10 List” — a perfect fit for a year that gave us more than enough moments worthy of being ranked, remembered, debated, and laughed about for years to come. Among the instant classics was “Cooking with Quinn,” which quickly earned its place in Hipster history.

Hunter Osgood made his first Hipster appearance — way to go Mom and Dad, Gil and Chase! Not only did Hunter join the crew, but he also got his first four-wheeler ride, officially beginning his Vermont adventure career early.

The pond was alive with competition as Quinn and Suzanne squared off in a legendary “Frog-Off,” catching frogs from the pond and keeping the kids — and probably more than a few adults — fully entertained.

The Bartletts — Julie, Jon, Bridgette, and Brexton — arrived for their first Hipster, adding new energy, new stories, and new faces to the growing Hipster family.

Hipster 2023 also marked the arrival of more next-generation Hipster energy, with Jane Semple and Viv McGovern joining the growing story of babies, toddlers, cousins, friends, and future mountain climbers who would carry the tradition forward.

And then came the surprise no one saw coming: the Cotter kids — Thomas, Matthew, and Suzanne — pulled off a full-blown coup with a surprise 30th anniversary celebration for Sue and Brendan. Wow. A true family moment, wrapped inside the greater Hipster weekend, and one that now feels even more meaningful with time.

Of course, Uncle Dave from Florida made the trip north, and Footie was there, as always, to enjoy the fun, the family, and the fire. And in another great Hipster surprise, Michael McGovern surprised everyone with a Vermont visit from his beloved Colorado, proving once again that the pull of Jay, family, and Hipster weekend can reach across the country.

Bailey and Libby — the nurses and Saint Anselm's classmates of Suzanne “Suz” — came ready to take on Jay Peak, proving once again that Hipster always finds a way to bring old friends, new friends, family, and mountain spirit together.

The side-by-sides were out in force, with RJ and Dillon taking the Can-Am for a ride, adding a little horsepower to the weekend. And in one of the great ceremonial moments of Hipster history, Kevin McGovern passed the legendary “jean overall cutoffs” to Liam Cotter — a transfer of tradition, fashion, and questionable judgment all at once.

There were pond swims, good eats, bonfires, great friends, endless laughs, and a Top 10 List full of moments that could only happen at Hipster — all the ingredients that keep the tradition alive.

But looking back now, Hipster 2023 became much more than another year of mountain memories. It became a pivotal reminder of just how fragile life can be — and how amazing, resilient, and mysterious the human body truly is.

Little did I realize that in just a little over a month, on September 25, 2023, I would be undergoing open-heart surgery and a triple bypass. As I pored through the photos from that weekend, I often wondered how close Hipster 2023 may have come to being my last.

That thought is both humbling and powerful.

Because Hipster has always been about more than a hike. It has always been about family, friends, movement, mountain air, laughter, loyalty, and the choice to keep showing up. In 2023, those things took on a deeper meaning.

What looked at the time like another great Hipster weekend now stands as a marker — a moment before life changed, before surgery, before recovery, before the fight back. It became a reminder to never take the people, the place, the mountain, or the moments for granted.

And in true Hipster spirit — with fight, faith, family, friends, and a whole lot of Vermont grit — Hipster 2023 was not the last.

The fires kept burning. The mountain stood tall. The family gathered. The next generation arrived. The Top 10 List grew. And the Hipster tradition lived on.

Hipster 2022 was a year full of sunshine, laughs, music, and celebration.

It was also the last year of Ben Farney music, with Ben set up on the gazebo overlooking the pond — a perfect Vermont backdrop for a perfect Hipster day. Ben had become a welcome sight at so many events and Hipster Hikes over the years, and his music helped define the feeling of those gatherings: relaxed, joyful, familiar, and full of heart.

This was also the year we celebrated Mary Price Maddox — history teacher extraordinaire and longtime leader at Acton-Boxborough High School. Mary had finally gotten her Jeep, at long last, and with a little Taylor Swift spirit in the air, it only felt right that the Hipster 2022 logo featured a Jeep climbing Jay Peak with the top down.

The slogan said it all: “Go Topless!”

Congratulations, MPM — or, as Jimmy Kelly calls her, “MGM!”

Hipster 2022 also brought a great visit with our new Cleveland crew friend, “Chaffy Assad,” who quickly became part of the wider Hipster family.

It was a warm, beautiful day on the mountain — full of sunshine, laughter, music, friendship, and all the easy magic that makes Hipster Hike what it is.

Four weddings helped set the foundation for Hipster 2021.

Chase and Gil — October 17, 2020. Alexa and Kevin — June 12, 2021. Thomas and Natalie — July 30, 2021. Kelsey and Adam — October 9, 2021.

By the time the crew pulled into Jay Peak, the year already felt like a celebration on top of a celebration. Weddings, reunions, road trips, and the return of the Squad after the strangest year in recent memory. It was time for a ruckus.

Fresh off Thomas and Natalie's nuptials in Cleveland, the crew carried the momentum north to Jay. Joining them were the Mays — Deb and Dave — making their inaugural Vermont visit and attending their first Hipster Hike at Jay Peak.

The 2021 shirt said it best: HIPSTER SQUAD, 7th Annual, Hipster Ruckus 2021, “Enough Said.” It carried the initials of the wedding couples, the dates, and the diamonds — a wearable timeline of a year that refused to be quiet.

Hipster 2021 became more than a hike. It was a wedding-year celebration, a reunion, a Vermont welcome, and a full-blown ruckus. With the Squad back together and the mountain once again at the center of it all, there really was only one thing left to say:

Enough Said.

Hipster 2020 was a lean year.

COVID had changed everything. Across the country, gatherings were canceled, routines were broken, and Zoom became the new standard for staying connected. Even in Vermont, where life still seemed to hold onto a little more space and fresh air, the mood of the year was different. Uncertain. Strange. Quiet.

For the first time, Hipster almost didn't happen.

There was no new T-shirt design. No big rollout. No fresh logo. No full-squad energy. For many of the regulars, Hipster 2020 became one of those years that just could not happen the normal way. It felt odd in the history of the tradition — like the world had paused, and even Jay Peak had to wait.

But then came one of the true Hipster warriors.

Chase Osgood, who had missed 2019 because of adulting, obligations, and the hard choices that come with growing up, made a declaration: he was not missing Hipster again.

In true Chase fashion, the message was simple: “Hell no.”

That was all it took.

For the loyal, the committed, and the slightly stubborn, Hipster 2020 became a thing. Not because it was easy. Not because it was perfect. Not because the whole squad could make it. But because Chase brought the attitude that has always powered Hipster at its best: show up, keep moving, and don't let the year win.

The shirts were recycled from past years, which somehow made the whole thing even better. It became less about the gear and more about the grit. Less about the official plan and more about the people who refused to let the tradition disappear.

Hipster 2020 was smaller, quieter, and different from every year before it.

But it happened.

And because it happened, it belongs in Hipster history as the year the tradition survived — carried forward by loyalty, Vermont air, a few recycled shirts, and Chase Osgood's determined refusal to let the mountain go unclaimed.

A lean year, yes. But a legendary one.

Hipster 2019 may go down as one of the best years in the history of the hike.

By this point, Hipster was no longer just a family hike up Jay Peak. It had become a true summer institution — part mountain climb, part reunion, part comedy show, part fashion statement, and part legendary Vermont gathering. It felt like the entire squad was there, with new foundational favorites arriving on the scene, including Natalie May, Adam Semple, and Alexa Coulombe.

The only major absence was one of the pillars of Hipster history: Chase Osgood. Chase had other obligations that year — an early sign of adulthood, competing priorities, and tough decisions. But Hipster history could not possibly move forward without Chase in the record, so he was proudly photoshopped into the memories. No true Hipster legend gets left behind.

The 2019 shirt became one of the all-time favorites, especially beloved by Brian Cotter and his boys — Liam, Dillon, and RJ. The design was sharp, bold, and unforgettable: a sleeveless hoodie celebrating the great Hipster patriarch himself, Footie.

The message was simple and classic: 3-3-3. For Footie, it represented three wives, three children, and three grandchildren — a perfectly Hipster tribute to a man whose life, humor, and presence had become part of the fabric of the gathering.

But 2019 was also a year of firsts. Most notably, Jim Harer made the commitment to the mountain. Hiking alongside Jim Kelly and Brendan Cotter, Jim came prepared for battle — armed with electrolytes, determination, and cans of oxygen. There may have been doubts. There may have been concern. Heather may not have been fully convinced. But Jim endured, climbed, and proved everyone wrong.

Jim crushed the Peak.

The pictures from that year were epic and, looking back, almost foreshadowed the great Hipster moments still to come. The energy was big. The cast was deep. The laughs were constant. The mountain had been earned.

And then there were the Hipster Warriors — Nick, JT, Harry, Ze, Justin, and even Cal Sullivan and Killian — all adding to the chaos, character, and spirit of the day.

Hipster 2019 had everything: the full squad, new legends, one photoshopped absentee, a beloved shirt, a tribute to Footie, a heroic summit by Jim Harer, and enough stories to carry the tradition forward for years.

It was not just another Hipster year. It was a highlight-reel year.

By Hipster 2018, the hike had officially become more than an annual climb up Jay Peak. It had become a full summer gathering — part hike, part reunion, part Irish-Vermont celebration, and part excuse for great food, loud stories, mountain music, and more than a few libations.

This was an epic year for the Hipster crew. The gathering continued to grow, welcoming a few amazing new people into the circle, including Emily Durette with Matt Cotter and Gil Collins with Chase Osgood. Each year, the group got a little bigger, the stories got a little better, and the tradition became more deeply rooted.

But Hipster 2018 also carried a special meaning because this year’s T-shirt celebrated Stephen Osgood, affectionately known as “Stinky.” Stephen’s famous slogan said it all:

If you grow up, you give up.

That line became more than a quote on a shirt. It became a reminder of one of the great truths behind Hipster itself: stay young at heart, keep moving, keep laughing, keep showing up, and never let age, responsibility, or the seriousness of life take away your sense of adventure.

Stephen always reminded the crew that there is strength in not taking yourself too seriously. There is wisdom in play. There is joy in being a little ridiculous, a little loud, a little stubborn, and fully alive. In many ways, “If you grow up, you give up” captured the Hipster spirit perfectly.

2018 was also remembered as the year of John Denver, mountain music, and the unforgettable discovery that Kevin McGovern apparently believed he could sing like Bradley Cooper. Whether the rest of the group agreed is still open to debate — but his confidence was undeniable, and the performance became another classic Hipster memory.

It was also the year of one of the all-time favorite Hipster shirts: the long sleeve. Comfortable, classic, and instantly part of the uniform, that shirt became one of the most loved pieces of Hipster history — made even better because it carried Stephen’s spirit and slogan with it.

By then, the Hipster Hike had found its rhythm. Some came to hike hard. Some came to socialize. Some came for the food, the laughs, the mountain air, and the people. But everyone came for the same reason: to be part of something that celebrated family, friendship, mobility, resilience, and the simple joy of gathering in Jay, Vermont.

Hipster 2018 proved that the tradition was no longer just about one comeback or one climb. It had become a yearly celebration of the whole squad — the Cotters, the McGovern families, the Kellys, the Osgoods, and friends — growing stronger, louder, funnier, and more legendary with every passing summer.

And through Stephen “Stinky” Osgood’s words, the crew had its marching orders:

Stay young. Stay moving. Stay laughing. Stay together.

Because at Hipster, growing older is allowed.

But growing up? Never.

On to Hipster 2017.

One year after the first official Hipster Hike, the tradition returned to Jay Peak with even more energy, laughter, and family pride. On Saturday, August 5, 2017, the Cotters, the McGoverns, the Kellys, and friends gathered for what was quickly becoming the social event of the summer.

The weather did not make it easy. The day was gray, wet, and mountain-chilly — the kind of Jay Peak weather that turns a hike into a memory. But that was part of the spirit. Rain jackets came out, boots got muddy, and the squad pushed forward together.

Hipster 2017 was no longer just about John McGovern’s comeback from hip replacement surgery. It had become something bigger: a celebration of mobility, family, friendship, Irish grit, Vermont toughness, and the joy of reaching the top together.

By the time everyone gathered at the peak, the rain had become part of the story. It was not a perfect summer day, but it was a perfect Hipster day — resilient, funny, damp, determined, and full of life.

The first official year of the Hipster Hike was born on a cold, rainy August day in 2016, the kind of Vermont day that tests whether a tradition is real or just an idea.

The sky over Jay Peak was gray. The trail was wet. The air had that late-summer mountain chill that sneaks into your bones. It was not the kind of day most people would choose for a celebration. But that was exactly why it became one.

This hike was never just about getting to the top of Jay. It was about John McGovern.

The year before, John had been battling a hip that was giving out on him. He was frustrated, limited, and feeling the weight of not being able to do the things he loved. The mountain, the outdoors, the simple freedom of movement — all of it felt farther away than it should have. But with encouragement, humor, family, and a brand-new pair of hiking boots bought at the Jay Country Store, John made his way up Jay Peak carefully, slowly, and stubbornly. Four hours later, sore but standing, he reached the summit.

That moment became the spark.

By 2016, John had gone through hip replacement surgery and was beginning the real climb back — not just up a mountain, but back into mobility, confidence, strength, and the rhythm of life. So the logo for the first official Hipster Hike captured exactly what the day meant: crutches crossed out, a mountain ahead, and a community refusing to let pain, surgery, age, fear, or weather decide what was possible.

On August 13, 2016, the squad climbed.

The rain came down. The wind cut across the trail. Jackets were zipped, boots were muddy, and the mountain made everyone earn every step. But the spirit of the group never broke. There was laughter, encouragement, checking in, waiting up, pushing forward, and the kind of shared toughness that only comes when family and friends are moving together toward something bigger than themselves.

And when John and the others reached the peak of Jay — nearly 4,000 feet above the valley — it was more than a summit. It was a statement.

Mike McGovern and Matt Cotter raised the Irish flag in celebration. In that moment, through the rain and cold, the flag became a banner for John, for the McGovern family, for the Cotters, and for everyone who had gathered around the idea that mobility is a gift and resilience is something worth honoring.

It was a celebration of new hips, old friendships, Irish pride, Vermont grit, and the stubborn joy of getting back up the mountain.

That day gave Hipster its identity.

The logo was not just a design on a shirt. It was a badge of survival. It said that the hike was about more than hiking. It was about overcoming. It was about family showing up. It was about friends refusing to let each other stay stuck. It was about taking the next step, then the next one, until somehow the summit comes into view.

The first official Hipster Hike was wet, cold, muddy, and unforgettable.

And from that rainy day forward, Hipster became what it was always meant to be: a yearly celebration of mobility, resilience, friendship, family, nature, and the belief that no matter what life does to your body, your spirit can still climb.

The idea for the Hipster Vermont Hike was born on July 18, 2015, during a summer visit to Jay, Vermont, when Colleen and John McGovern came to stay with Suzanne and Brendan Cotter at their Vermont home.

At the time, John was delaying a much-needed hip replacement surgery. He was frustrated, limited, and feeling the weight of not being able to do many of the outdoor activities he had always loved. Brendan, seeing both the frustration and the opportunity, said simply:

“John, let’s hike Jay.”

John pushed back at first. He said he didn’t have the “proper equipment.” No hiking boots. No real plan. No guarantee he could make it.

So Brendan and John went down to the Jay Country Store, where John bought himself a pair of hiking boots. And with that, the first unofficial Hipster Vermont Hike began.

They set out carefully, thoughtfully, and slowly up Jay Peak. It was not a race. It was not about speed. It was about movement, encouragement, patience, and the quiet belief that sometimes the first step matters more than the summit.

Four hours later, they reached the top.

John made it — sore, tired, and deeply tested. Nurse Colleen quickly tended to him with orange juice, salt, and the loving attention only Colleen could provide. But John had done it. He had climbed Jay Peak before his hip replacement, proving something to himself that would become the foundation of everything Hipster Vermont would later stand for.

That hike became a pivot moment.

In early 2016, John went on to have his hip replacement surgery. And in the years that followed, he became one of the front-runners of the Hipster Vermont hikes — steady, strong, consistent, and improving each year. What started as a slow and uncertain climb became a story of recovery, mobility, confidence, and friendship.

That day on Jay Peak was the genesis of the Hipster Vermont Hike: a celebration of family, movement, nature, friendship, and the glory of being outside together.

It was never just about hiking.

It was about getting back up the mountain — one step at a time.