What the Ski, Skate & Board Sale Brings to Our Community; and Who’s Making It Happen

Every November, as the leaves fall and winter begins to hint at its arrival, families across Hamilton, Wenham and the North Shore prepare for one of the community’s most beloved traditions: the Ski, Skate & Board Consignment Sale. For more than a decade, the sale has helped families outfit themselves for the season without breaking the bank; while also giving neighbors a chance to connect.

This year, the effort is being led by Jeannine Ryan, a longtime Hamilton resident and mother of three, who also works as a registered nurse on the North Shore. Thanks to her long standing leadership and a new partnership with the Friends of Miles River Middle School and Hamilton-Wenham Regional High School, the sale will return November 15–16, hosted in the high school gym.

For Ryan, the sale is much more than a marketplace. It’s a way to open doors, reduce barriers, and strengthen community ties.

From Brooklyn to Hamilton

Ryan’s journey to Hamilton began in the bustle of New York. Originally from the Hudson Valley, she met her husband Patrick while living in Manhattan. After moving to Brooklyn and welcoming their first daughter the couple realized city life was starting to feel small. With Patrick working remotely, the couple relocated to the North Shore, near some family members who had already settled in the area.

The transition wasn’t seamless. “Initially it was overwhelming,” Ryan recalls. “We hadn’t driven a car in five years, so just getting used to suburban life was a lot.” But as extroverts, both she and Patrick quickly plugged into the community, joining the Mothers’ Club and finding their footing. Over time, their family grew to include three daughters; one in college;  a high school junior; and the youngest an eighth grader.

Finding Winter Identity

Although Ryan hadn’t grown up skiing, Patrick had. With three energetic young girls packed into a small house, the family needed a winter outlet to beat the cabin fever so familiar to New England families. They started with lessons at Ski Bradford. Soon, skiing became not just a pastime but a way of life.

“In the winter, we are skiers,” Ryan says with a smile. “For the girls, it’s their identity as winter athletes. Last year they skied about 60 days. Their friends are from the ski community. We’ve made lifelong friendships through skiing.”

At first, Ryan had a choice: learn to ski or stay home. “It was trial by fire,” she laughs. Now, while she admits she can’t keep up with her daughters, she enjoys the sport and the camaraderie it brings. The family spends most weekends in New Hampshire fully immersed in the skiing lifestyle.

The Birth of the Sale

Ryan didn’t start the Ski, Skate & Board Sale, but she has been part of its story since day one. The sale began in 2012 at Cutler Elementary School, launched by Hamilton baker Carol Harlow-Carlson, owner of Treat Cakes and Confections, who combined fundraising with practical community support.

Ryan was a new mom at the time, eager to get involved. She volunteered the very first year and never left. “It was a big school fundraiser, and the way I fell into it was just trying to meet people,” she says. “That’s how it happened.”

When Carlson eventually stepped back, Ryan and fellow parent Dabney Brown Smith stepped forward to co-chair. Together, they grew the event, retaining vendor partnerships with businesses like Wenham Sports Stop, Hardy’s Ski Emporium and Plymouth Ski & Snow that Carlson had secured. Over the years, it expanded from a small school fundraiser into a regional resource for families looking to buy and sell winter gear.

Breaking Barriers

For Ryan, the true power of the sale lies in its accessibility. Skiing and hockey are notoriously expensive sports, requiring hundreds; sometimes thousands; of dollars in equipment just to get started. The consignment sale changes that equation.

“What’s always been important about the ski sale is that it allows access into sports that can be cost-prohibitive,” Ryan explains. “You can buy a used pair of skis for $40, and if it doesn’t work out, you can resell them the next year. It gives families a chance to try something new.”

There’s also a strong sustainability component. “Sometimes it’s all about new, new, new,” Ryan says. “But this is about reusing, recycling, keeping quality gear in circulation instead of in a dumpster. Some kids grow out of gear after one year and there’s plenty of life left in the item.  It’s social consciousness and community-building all in one.”

The event’s final day, when many prices are slashed by 50%, often provides the most poignant moments. “It feels good to see families outfitting their kids in snow pants, boots, gloves, for a fraction of the cost; but still getting great quality,” Ryan says.

The Year Without

In 2024, after more than a decade at Cutler Elementary, Jeannine’s daughters, and many children of longtime volunteers, had moved on from the school. With that transition, the Ski, Skate & Board Sale also came to a pause. The Friends of Cutler shifted their fundraising focus to a new event, the Turkey Trot, a student-centered celebration that quickly became a cherished tradition and successfully raised ample funds to support enrichment programs.

Yet even as the community embraced this fresh direction, the absence of the Ski, Skate & Board Sale was keenly felt. Families who had come to rely on it for affordable winter gear missed it deeply. “People kept asking me, ‘Where’s the sale?’” Ryan recalls.

That gap sparked new conversations. Leaders from the Friends of Miles River Middle School and Hamilton-Wenham High School approached Ryan with the idea of reviving the sale at the regional schools. Energized by their enthusiasm, she agreed. “Yes, it’s hard work,” she admits, “but it’s a short burst of work for a big community benefit.”

Importantly, the Friends of Cutler remain enthusiastic champions of the event, even as their fundraising priorities have evolved. As Co-president Emily Puopolo shared: “We’re thrilled that the ski sale is coming back this year! Friends of Cutler is proud to support the cause; we’ve donated all our ski sale gear from clothing racks to ski racks, and we’ll be encouraging everyone to shop the sale!”

This year, with support from the Friends, veteran volunteers, and new parents alike, the sale is back, and bigger than ever.

What’s New in 2025

The biggest changes this year are the venue and the fiscal beneficiary. Instead of being spread across multiple spaces at Cutler Elementary, the sale will fill the high school gym, creating one central, buzzing hub. Shoppers can expect the same mix of consignment and donations, alongside vendor partnerships that bring in new gear. Proceeds will go to the Friends of Miles River Middle School and High School and support teachers and students field throughout the school year. 

Ryan encourages families to start sorting their closets now and to follow the sale’s Instagram or Facebook pages to learn how to consign or donate. “Look for jackets that don’t fit anymore, skates in good condition, skis that are still safe,” she advises. (Consignment items are carefully checked against industry safety lists to ensure bindings are up to standard.) “We’ll take anything winter-oriented: snow pants, gloves, hats, boots; if it helps someone get outside, we want it.”

While donations are particularly valuable since the schools keep 100% of those sales, consignment remains an important part of the event. Either way, every item helps outfit families and support the community.

More Than a Sale

At its heart, the Ski, Skate & Board Sale is not just about equipment. It’s about connection. It’s about families finding affordable ways to embrace winter together, neighbors working side by side, and the joy of a shared seasonal tradition.

“There’s this perception that Hamilton is a super wealthy town,” Ryan reflects. “But that’s not the reality for everyone. This sale helps level the playing field. And it builds community; because when people come together for something like this, it’s about more than just shopping. It’s about supporting each other.”

Thanks to Ryan and the many volunteers who will give their time, the sale will returns this year and countless families across the North Shore will find themselves better prepared to embrace winter; with skis, skates, boards, and a sense of belonging.

As Ryan likes to say: “Think snow.”