Volume 1 — Issue 6 — September 2026

Sail Salem relies on a network of city leaders, dedicated park staff, and school partners who care deeply about the kids in our community. 

As another season comes to a close, we want to take a moment to shine a light on some of the incredible people and organizations who support our mission, keep our water access running smoothly, and work to ensure every family has a chance to participate.

Winter Island—A Special Home

For nearly two decades, Winter Island has been the home of Sail Salem and an important part of our identity. Its location on Salem Harbor provides our young sailors with an extraordinary setting in which to learn, not only how to sail, but also how to respect the water, work together, build confidence, and become part of Salem’s maritime community.

Our success at Winter Island is thanks to the dedicated team at the City of Salem who welcome us back each year to make our summer program a success.

We are especially grateful to Parks and Recreation Superintendent Trish O’Brien and Program Manager Kathy McCarthy for their continued cooperation, encouragement, and support of Sail Salem and our young sailors.

We have also been particularly fortunate to enjoy close and longstanding relationships with Salem Harbormaster Bill McHugh and Winter Island Manager Dave Gilbert.

Bill has been a valued friend and partner to Sail Salem, sharing his knowledge of Salem Harbor and helping us operate safely and responsibly on the waterfront. Bill and the Harbormaster’s Office understand what we are trying to accomplish, giving young people the opportunity to experience, understand, and appreciate the harbor that is such an important part of Salem.

Our relationship with Dave Gilbert has been equally special. As Winter Island Manager, Dave has worked closely with Sail Salem year after year. Whether helping us prepare for another season, solving the inevitable problems that arise during a busy summer, or simply offering advice and a helping hand, Dave has always been there for us.

Dave will retire next year, and his retirement will mark the end of an important era for Sail Salem at Winter Island. We will miss having him as our neighbor and partner, and we are enormously grateful for his friendship, cooperation, good humor, and many years of support.

As Sail Salem approaches its 20th anniversary, Winter Island remains central to both our history and our future. We look forward to continuing our partnership with the City of Salem, Parks and Recreation, the Harbormaster’s Office, and the Winter Island community—and to ensuring that generations of young people continue to have the opportunity to experience Salem Harbor from the water.

To Trish, Kathy, Bill, and especially Dave as he approaches his retirement: thank you for welcoming Sail Salem to Winter Island and for being such an important part of our story.

Partnering with Salem Public Schools 

One of Sail Salem’s most important goals is making sure that financial circumstances do not determine whether a Salem child has the opportunity to experience Salem Harbor.

An important part of that effort is our relationship with Salem Public Schools. We work closely with Liz Yoder and the City Connects coordinators, along with Sail Salem Board member Brad Maloon, an On Point/Summit teacher at Collins Middle School and Salem High School. Together, they help us reach families who might not otherwise know that sailing and scholarship opportunities are available.

These educators know their students. They can recognize young people who would benefit from attending camp at Sail Salem,  and they help introduce families to an opportunity that may be completely new to them.

That personal outreach makes an enormous difference. Simply offering scholarships is not enough. We need trusted teachers, coordinators, and school professionals who can connect us with the young people those scholarships are intended to serve.

In 2026, Sail Salem provided 26 young people with scholarships covering 44 weeks of summer sailing. Our partnerships with Salem Public Schools and City Connects help ensure that those scholarships reach Salem children who can benefit from them.

For these young people, Sail Salem is about much more than learning to sail. Time on the water provides opportunities to develop confidence and independence, learn teamwork and responsibility, make new friends, and experience Salem Harbor as part of their own community.

It also gives our sailors a greater understanding of the marine environment and the importance of protecting it. Through time spent on Salem Harbor and Salem Sound, our young people learn about the wind, weather, tides, marine life, water quality, and the impact people have on our coastal environment. We want them not only to enjoy the harbor today, but also to understand their responsibility to protect and preserve it for future generations.

As Sail Salem approaches its 20th anniversary, expanding access and opportunity—and developing the next generation of responsible stewards of Salem Harbor—remain at the heart of our mission. We hope to strengthen these relationships and reach even more Salem students in the years ahead.

Our thanks to Liz Yoder, the City Connects coordinators, and Brad Maloon and the On Point/Summit programs at Collins Middle School and Salem High School for helping us open Salem Harbor to more of Salem’s young people.

Fundraising Event Wrap-Up: the
Sail Salem Labor Day Pursuit Regatta at BYC

On Labor Day, Boston Yacht Club generously hosted its annual Sail Salem Pursuit Regatta, with all net proceeds donated to our organization.

It was a beautiful, sunny day on the water! We had our highest participation rate in recent years with 35 boats at the starting line. Indra (Skipper Kim Breed) took first place in the Spinnaker Division and Exocet (Skipper Kevin Taylor) won the Jib & Main Division…

We Care!

Sustaining the ocean and protecting the local coastline is vital to our mission. Our STEAM education program teaches responsible stewardship of our marine environment and is an important part of our camp curriculum.

Providing Unforgettable Experiences

Sail Salem connects our community to the sea through historic sailing, maritime education, and hands-on experiences on the water. Your donation helps maintain our watercraft and equipment and expand our STEAM educational program. Every gift helps keep our sails full and our mission moving forward.

Our community is the wind behind our sails.
Thank you for being a part of it!

Sail Salem does not discriminate on the basis of race, color, national origin, religion, gender, familial status, disability, ancestry, age, marital status, public assistance status, veteran/military status, or genetic information and is funded, in part, by the City of Salem Department of Planning & Community Development and the U.S. Department of Housing & Urban Development.