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Over winter break, one of our Founding Students and Young Innovator Award recipients, Sierra S-B. ’21 was admitted Early Decision into Wake Forest University. Sierra, who is our SGA co-president, has taken advantage of many of our ColLAB offerings like our service trip to Puerto Rico. She is excited to continue her journey at Wake Forest stating, “Wake Forest University offers many exciting internship opportunities to explore my interest in medicine.” 

To learn more about our approach to College Counseling, check out our Better Outcomes and College Counseling pages.

While our students tell us the first time they stepped on campus they know The Winchendon School was special because of the community they discover here, we know it’s what they do while they are here that truly makes the School a special place.

In this video, three recent alumni talk about what they did while they were here and how The Winchendon School transformed the way they looked at school. All three students transferred to Winchendon, but that’s about all they have in common. From home-schooler, to a student with school anxiety, to transferring from a prominent school for students with language-based learning differences, each one found a purpose here.

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This article first appeared in New England Baseball Journal and is republished here with permission.

The first time John Toffey walked onto the Winchendon School campus in late 2018, he knew right away there was much work to be done. Toffey came to this Central Mass. community, which hugs the New Hampshire border, with a highly regarded reputation of coaching excellence. He was looking to bring that same kind of success here.

In his previous stops at Salisbury School and Cheshire Academy, Toffey engineered both programs into fine-tuned baseball machines. At Winchendon, some felt the idea of him turning this lackluster program into something identical seemed like a bit of a reach. Prior to his arrival, Winchendon was perceived more as being a junior varsity level program, playing a limited number of games, with no fall season and no preseason trips. In essence, you could say everything was against Toffey. Yet Toffey thought otherwise.

Orchestrated with careful precision and well-planned objectives on how things needed to be done, Toffey immediately went to work. From the outset, he cast zero doubts that he could achieve a comparable scenario here to the ones he left at Salisbury and Cheshire.

Also serving as the school’s Director of Admissions, Toffey left no stone unturned when it came time to seek out talented, well-adjusted student-athletes to buy into what he was trying to build at Winchendon, in addition to his tireless efforts of transforming it into a reputable and respected program.

In Toffey’s first season in 2019, he made it work. Toffey sold potential players on the school’s elite academic programs, its rural campus environment and the opportunity to turn Winchendon into a legit prep power. That season, Toffey brought in 15 players, which paid off mightily. The team finished 20-6, capped off by a NEPSAC New England Small School championship. Over the past three years, the school has sent over 30 players to high level college programs, including such notables as pitchers Jake Gigliotti (Northeastern University), Jackson Bright (Wesleyan University), catcher Max Walker (UMass-Lowell) and outfielder/second baseman Phil Bernstein (Hamilton College) — just to name a few. In addition, former ace hurler Nate Espelin was selected in the 35th round of the 2019 MLB draft by the New York Yankees, but instead, chose to attend the University of Dayton.

An outstanding former student-athlete in baseball and hockey at St. Sebastian’s School, Toffey, a Barnstable, Mass., native, went on to star in both sports at UMass Amherst. It was there where he was drafted by the Colorado Rockies in baseball and the New Jersey Devils in hockey. Toffey chose the latter, playing three seasons in the Devils organization. Growing tired of trolling through the minor leagues with reasonable uncertainty, Toffey came to the conclusion that it was time for a change.

He left hockey to accept an assistant baseball coaching position at Salisbury in 2008 under the tutelage of current Kansas City Royals scout Mark Leavitt. At the start of 2009 season, Leavitt was offered and accepted an assistant coach/recruiting coordinator position at Stetson University. His departure opened the door for Toffey to take over an already thriving program.

Yet, once again, his mind told him there was still more work to be done. One of Toffey’s first acts as head coach was to expand the Salisbury roster. He brought in a bunch all-star caliber individuals to back up another set of all-star players. In his seven seasons at the helm of the Crimson Knights, Toffey’s teams won an unprecedented six WNEPBL titles, including four straight. In 2014, the club finished with an astonishing 33-1 record, and was ranked eighth nationally by Perfect Game.

Toffey opted to leave Salisbury and face a new challenge at Cheshire. What was then expected to be a reclamation project proved otherwise. In his three seasons managing the Cats, they won two WNEPBL championships. His overall record at both schools is a mind-boggling 135-9. With Toffey’s first season at Winchendon in the books, that overall mark now stands at 155-15.

“Each place I have gone has been a little different,” Toffey explained. “At Salisbury, Dan Donato really got that program going (in the early 2000s). He got that thing firing at a very high level. When Dan moved on to Dexter Southfield, Salisbury hired Mark to keep it going, which he certainly did. When I took over, the program had already been built up, and I was just trying to keep things going at a high level.

“When the opportunity at Cheshire opened up, I made a decision. It was more of a rebuilding of the program when I first arrived. A few of the other athletic teams at the school were pretty strong, but in terms of baseball, it was more about being proactive in admissions and recruiting kids who wanted to come to the school to play baseball. We were fortunate to build it up pretty quickly.

“Here at Winchendon, we immediately let families know that we were going to be starting up a really competitive baseball program. We definitely brought in some really good players that first year. It was a great group of kids who decided to take a chance on something that was new here.”

That philosophy appears to be resonating quite well at Winchendon as a growing number of potential student-athletes have shown considerable interest in wanting to attend here either as an underclassman, upperclassman or a post-graduate. Former Boston Latin High School standout Nick Pappas is one of them. After graduating from Latin in 2019, Pappas didn’t feel he was fully ready to handle the rigors of college life. Pappas, who hails from West Roxbury, Mass., made an open house visit to Winchendon and immediately fell in love with the school. The second baseman has only been on school grounds since the fall, but recognizes his decision to enroll here was the correct one.

“When I first came here, I saw how close everything was to one another whereas when I attended Boston Latin, I had to take the commuter train into Boston every day,” he said. “I felt like I was right at home here even before I began classes. When I got here, I found things to be very stringent which was perfect for me. The campus had everything I was looking for. All of the facilities are right there which was something I was missing at Boston Latin.”

Pappas says the learning environment at Winchendon has been nothing short of ideal for him. The class sizes are small (usually fewer than 10 students), the teachers take a special interest in all of their students, and by living on campus, it has allowed him to mature and become more independent.

“I believe coming to a school like this, and getting that extra year to raise my grades as well as physically and mentally maturing more, has been extremely important,” said Pappas, who is interested in studying business and is currently leaning towards Bentley University. “My parents have already seen a big difference in my maturity since I’ve been here. That is such an important aspect to have going into college in terms of taking everything head on.”

As a coach, one of Toffey’s prime directives has always centered around putting his players in situations comparable to college. He also cites the preparation offered to all students makes the transition to college a lot less stressful.

“A majority of the kids who leave here to enter college are better prepared academically, socially and of course, from a baseball perspective,” he said. “Many top level programs tend to focus more on those types of kids during the recruiting process. My hope is that college coaches know they are getting kids they can rely on and will continue to want those types of kids from our programs here.”

For baseball players, Toffey can now market his program as being a legitimate New England power as well as providing an opportunity to move on and play at the collegiate level.

“I think when you have success, people are attracted to that,” Toffey said. “I think people are now starting to look at us and see the colleges these kids are going to and the success they are having. It is also important that we develop some great relationships with many college coaches. So, when families look at Winchendon, they see it as being a phenomenal school that is personalized with small class sizes. And if their son is interested in playing baseball, we have started to build a great program here to which the school is fully committed to.”

Of his three stops, Toffey realized Winchendon would most likely be his biggest challenge by far in terms of getting the program off the ground, assuring kids that this was a good landing spot for them, and making people aware of Winchendon’s well-founded academic reputation. He also knew that some people may not even know where the town of Winchendon is located.

“Once you come here, you soon discover it to be a beautiful location and I can’t think of any other place I would rather be to raise my own family than here,” Toffey said.

By John McGuirk December 14, 2020