By Tiffany Williams –
STURBRIDGE, Mass. — About 59 miles west of Boston sits the town of Sturbridge, population 9,867. It’s the kind of New England town known for its colonial roots, historic charm and the sort of Main Street where people still wave as they pass by.
It’s also the kind of place where girls’ softball isn’t just an after-school activity. It’s tradition. It’s teamwork. It’s community stitched together by volunteers, parents and neighbors who show up.
This week, that tradition got a boost.
The WooSox Foundation — the charitable arm of the Worcester Red Sox — rolled into town with its Care-A-Van and a check for $3,000 for Sturbridge Girls Softball. The money will cover registration fees for more than 30 girls, ensuring they can take the field this season.
But the check was only part of what was delivered.
The real delivery was opportunity.
The gift came through Tyler’s Teammates, a program created in 2022 by Steve and Lynn Trudell to honor their 13-year-old son, Tyler, who peacefully passed away in his sleep on May 13, 2021. Tyler, a Paxton Little Leaguer, loved baseball and adored his teammates.
From unimaginable loss came a mission.
The Tyler’s Teammates initiative provides equipment and registration funds to organizations and individuals who might not otherwise be able to participate in Diamond Sports. According to Little League Baseball and Softball, one in five children may not have the opportunity to play sports due to financial challenges.
That’s not just a statistic. That’s a child sitting on the sidelines.
“The Tyler’s Teammates program holds a special place in the hearts of everyone at the WooSox, and we all take pride in being a small part of Tyler’s legacy,” said Emerson White, Manager of Community Relations & the WooSox Foundation. “We’re grateful to Lynn and Steve for their continued partnership and the love they pour into giving local youth the opportunity to play baseball and softball.”
The WooSox Foundation first announced its partnership with the Trudell family on Valentine’s Day in 2022 at Paxton Center School. Tyler’s eighth grade classmates and teammates — with whom he played for eight years — were named ambassadors of the program and received custom T-shirts and certificates.
Since then, Tyler’s Teammates has quietly gone about its work — covering fees, supplying equipment, opening dugout doors.
In Sturbridge, softball is more than a sport. It’s a cornerstone for personal growth. It teaches resilience when you miss the ball. It teaches courage when you step into the batter’s box. It teaches belonging when teammates call your name.
On Friday, the WooSox Foundation wasn’t just presenting a $3,000 check. They were presenting cleats on fresh dirt. Gloves snapping shut. Parents cheering from aluminum bleachers.
Earlier that same day, the Care-A-Van made other stops across central Massachusetts.
First, at El Buen Samaritano in Worcester, a mission-driven organization that feeds families while offering support services designed to help Worcester residents thrive.
Then, at the Worcester Senior Center, where WooSox Foundation members delivered roses for Valentine’s Day, bringing a little color to a winter afternoon.
The Foundation’s work focuses on education, social justice, conquering cancer and recreation. Its Diamond Sports initiative encourages children to live healthy lifestyles and learn the values that sports teach — whether it’s baseball, softball, Wiffle Ball or kickball.
Since their first season in Worcester, the WooSox have embedded themselves in the community, giving back in ways that don’t always show up on a scoreboard.
When the Care-A-Van drives through central Massachusetts, it carries more than staff and supplies. It carries intention. It carries memory. It carries Tyler.
Lynn Trudell, Tyler’s mother, crafts and sells bracelets to help fund the program. The bracelets are sold online and in the Team Store at Polar Park. Each one is small enough to fit around a wrist — and strong enough to help keep a legacy alive.
Organizations and families hoping to join Tyler’s Teammates can apply through the WooSox Foundation.
In towns like Sturbridge, where softball fields double as gathering places and summer evenings stretch long past sunset, opportunity can change a childhood.
On Friday, more than 30 girls moved one step closer to taking the field.
And somewhere in the crack of a bat and the cheer from a dugout, a 13-year-old girls’s love of the game lives on.
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Laura Soukkavong contributed to this story.