Head to any yacht club in a relatively populous area, and the youth program director will have a healthy list of regattas that their young sailors can travel to compete in. They offer challenge, camaraderie, and a chance to learn about sailing in a new venue. But with so many options and so few summer weekends, how do you choose?
For three decades, the Cottage Park Yacht Club in Winthrop, Massachusetts has hosted one such regatta—but with a special mission. In 1995, Peter Costa, Joseph Zambella, and Peter Rodriguez hoisted the sails on what would become the club’s proudest tradition: the Make-A-Wish Regatta, named for the charitable foundation that grants wishes to children with life-threatening health conditions. Raising $9,000 in its first year, the regatta was able to sponsor three children’s wishes. It has only grown from there.
“It’s so easy to make a family smile,” says race chair and former commodore John Cataldo. “I was ill myself 20 years ago, and I know that feeling. I know what it’s like to sit in a hospital just waiting for something to smile about. And when we do this, these kids have something to smile about again.”
John took over running the regatta four years ago and has ramped up the fundraising efforts each year since, now including a raffle, auction, and a dinner that bring in sailors and non-sailors alike. “They enjoy it,” he says of the participants, from youth racers to club volunteers. “And they show up because they believe in it. All this is donated from community members and local businesses.”
Though most of the competitors are kids taking to the water in dinghies, the regatta also has a Snipe class and a pursuit race for the bigger boats, charting a scenic and challenging course through the Boston harbor islands.
The youth sailors, who stay closer to the club, also have some dynamic scenery to look out for. Boston Logan International Airport’s runway has planes taking off nearby. Several times an hour, an airplane roars overhead, spitting out a gusty downdraft—and occasionally taking out boats like dominoes, one after another. The random chaos adds a bit of fun for the out-of-towners who aren’t used to it, and it’s worth a visit to the area just to see the spectacle of the low flying planes.
This year, the club was proud to announce that the regatta has raised a cumulative one million dollars for Make-A-Wish Massachusetts and Rhode Island. It is among the longest-running and most successful community events supporting the organization, and Cottage Park was recognized in 2025 with the charity’s Community Hero Award
“With any Make-A-Wish event, you know that every cent and every dollar is going to giving a kid their dream,” says Courtenay Worcester, a speaker at the regatta’s Saturday night reception whose four year old daughter, Elise, was a wish recipient earlier this year.
Courtenay remembers difficult months of leukemia treatment, and worrying about her daughter’s health and future while also worrying that she was missing out on her young son’s early years. After princess stories became central to Elise’s treatment—hold still like Anna from Frozen, be brave like Merida—her wish was to go see their castle, to visit Walt Disney World Resort. The family made the trip in February and say it was an experience they will never forget, where the children could just be children without worrying about the weight of everything else for a while. “There is nothing that we could do to return the favor. I’m honored to be here to share our story and share the impact being made here.”
“In the face of life-threatening medical conditions, wishes enable children to experience profound joy, renewed resiliency, and lasting hope. We can’t grant wishes without terrific community partners like Cottage Park and its members,” says Caroline Craig, Make-A-Wish community partnerships coordinator. “The achievement of hitting one million dollars raised is so joyous, and we’re utterly grateful to this community and their continued support. With 650 local children currently qualified for and awaiting a wish, partners like Cottage Park are vital to enabling us to reach every eligible child.”
Years of work have gone into hitting this milestone, and for the organizers, it’s just the beginning. Cottage Park has created a regatta with a mission, and that vision for joy and hope permeates the entire event, ensuring that it will carry on for years to come. As John puts it, “It’s a regatta that once you go to it once, you come back every year.”
For more about Make-A-Wish’s program, visit massri.wish.org.
