For half a century, Chesapeake High School has been part of the fabric of Pasadena.
Next week, students will return to Chesapeake’s hallways for a particularly meaningful school year, as the Pasadena high school marks 50 years since first opening its doors in 1976. The milestone offers an opportunity not only to celebrate five decades of Cougar pride, but also to look back at why Chesapeake was built, how the school has evolved and the lasting role it has played in the Pasadena community.
The story of Chesapeake High School begins during a period of tremendous growth for Pasadena.
Before Chesapeake existed, Northeast High School was Pasadena’s only public high school. As residential development spread across the peninsula and the number of school-age children increased, Northeast became increasingly overcrowded. By the 1970s, the growing student population made another high school a necessity. Chesapeake was built to divide the community’s expanding high school enrollment and give thousands of families on the eastern side of Pasadena a school closer to home.
In many ways, Chesapeake’s creation reflected what was happening throughout Pasadena at the time. Neighborhoods were expanding, new homes were appearing across the peninsula and what had once been a much more rural collection of waterfront communities was steadily becoming the suburban Pasadena recognizable today.
The new high school was constructed at 4798 Mountain Road in Lake Shore, on the property of George Jenkins and John Ellison. At the time, the community largely protested the location of the new school, stating that the complex was too close to the tip of the peninsula and would complicate traffic. Despite the protest, the school was built with the mission of bringing in students from communities tucked between the Magothy River, Bodkin Creek and the Chesapeake Bay. The geography of the area has always helped give the Chesapeake feeder system its own distinct identity within Pasadena.
Leading the new school was Dr. William H. Norman, Chesapeake High School’s founding principal.
Norman served as principal from the school’s opening in 1976 until 1983 and played an important role in establishing Chesapeake’s identity during its earliest years. He was remembered as a leader who valued teamwork, fairness and maximum productivity, helping shape the culture of a school that was building its traditions from the ground up.
Nearly three decades later, tragedy brought the Chesapeake community together once again to remember its founding principal. Norman was tragically killed at the age of 76 in Tampa, Florida, in 2011.
The following year, students, staff, parents and alumni gathered at Chesapeake High School for a special rededication of the auditorium in his memory. The 2012 ceremony celebrated Norman’s life and legacy while reaffirming the significance of the William H. Norman Auditorium – a space that continues to connect today’s students with the man who helped guide Chesapeake through its formative years.
His influence remained so significant that Chesapeake’s auditorium was later named the William Norman Auditorium in his honor. A portrait of the school’s first principal has also hung inside the auditorium, preserving a connection between generations of students and the administrator charged with leading Chesapeake when there were no traditions yet to inherit.
From the beginning, Chesapeake also had the task of creating something harder to construct than classrooms and athletic fields: an identity.
The Cougars became the school’s mascot, and blue and gold became its traditional school colors. Over time, Chesapeake and Northeast developed one of Pasadena’s most familiar rivalries, fueled by the fact that the two schools serve different portions of the same tightly connected community.
For local families, that rivalry can run through generations – and sometimes even through the same family.
But Chesapeake quickly became a community of its own.
Its feeder system developed around Chesapeake Bay Middle School and elementary schools serving communities throughout the eastern Pasadena peninsula. Today, Chesapeake remains one of Pasadena’s two public high schools and serves students in grades nine through 12.
Athletics have also played a major role in shaping Chesapeake’s identity over the past 50 years.
Generations of Cougars have represented the school on fields, courts, mats and tracks, and Chesapeake has built an impressive championship tradition along the way. The school’s teams have captured at least 15 MPSSAA team state championships, led by one of the most successful softball programs in Maryland history. Chesapeake softball has won eight state titles — in 1988, 1990, 1991, 1992, 1993, 2007, 2008 and 2021.
The baseball program has added three more state championships, winning in 1997, 2014 and 2022. The 2014 championship was Chesapeake’s second baseball title and its first in 17 years, while the Cougars captured their third in 2022 with a 5-1 victory over Towson in the Class 3A state final.
Chesapeake wrestling has also enjoyed considerable success, winning state team championships in 1981, 2000 and 2002. The 1981 team helped establish that tradition early in the school’s history, capturing a state crown just five years after Chesapeake opened.
That championship legacy has been built not only by athletes and coaches, but also by the people who have helped oversee Chesapeake’s athletic program through the decades.
Al Grau served as Chesapeake’s athletic director during the early 2000s, a period when the school was managing a large and active athletics program amid enrollment that was approaching 2,000 students. By 2002, Grau was representing Chesapeake in broader discussions about the challenges facing high school athletics and the growing difficulty of recruiting teachers to also serve as coaches.
In 2004, Edward “Chip” Snyder took over as Chesapeake’s athletic director, beginning what would become a remarkably long tenure overseeing Cougar athletics. Snyder was already deeply connected to the program before becoming athletic director. A physical education teacher and longtime coach at Chesapeake, he previously coached varsity baseball and served as an assistant on the Cougars’ 1997 state championship baseball team. Chesapeake’s athletics website has also identified Snyder as the longest-tenured coach in the school’s athletic program.
More than two decades after taking the position, Snyder remains Chesapeake’s athletic director today. His tenure has spanned multiple generations of athletes, numerous state championship runs and significant changes to high school sports, facilities and game-day operations. He has also taken on leadership responsibilities beyond Pasadena, including serving as a regional director for the MPSSAA football state committee.
And Chesapeake’s championship story is still being written. During the 2025-26 school year, the Cougars added another major accomplishment when Chesapeake captured the Class 3A winter cheerleading state championship.
From championship softball dynasties and state-title baseball teams to wrestling, cheerleading and countless county and regional accomplishments, athletics have given generations of Chesapeake students another way to build the traditions and Cougar pride that have come to define the school over its first half-century.
The school itself has changed considerably during those five decades. At times, those enrollment demands were substantial.
Public enrollment records show Chesapeake had nearly 2,000 students during the early 2000s. Enrollment reached 1,938 in 2003 and remained around 1,900 for several years before gradually declining during the following decade. More recently, enrollment has begun climbing again, with the school serving roughly 1,500 students today.
That evolution has not been limited to the size of the student body.
Chesapeake has repeatedly adapted its academic offerings to meet the changing needs of students. In 2007, the school became home to what Anne Arundel County Public Schools described at the time as the first STEM Academy in Maryland, an initiative designed to strengthen opportunities for students interested in science, mathematics and technology.
Today, students can pursue opportunities ranging from computer science and Microsoft certification to Early Childhood Education, Culinary Arts and Chesapeake’s Information Management Signature Program. Athletics, robotics, music, theater, dance, student leadership and dozens of clubs provide another dimension to a school experience that looks considerably different from what students encountered in 1976.
Some Chesapeake programs have earned recognition well beyond Pasadena.
The school’s yearbook program, for example, developed a reputation for excellence. An earlier profile of Chesapeake noted that its student-produced yearbooks repeatedly received honors, with the 2003 edition earning such high recognition that it was used as a model by yearbook publisher Herff Jones.
Chesapeake’s performing arts programs have similarly created traditions spanning generations. In 2024, alumni whose years at Chesapeake stretched from 1984 through 2024 returned to the school to stage an alumni production of “Mamma Mia!” The show brought former Cougars from four decades together on the same stage – a fitting example of the kind of connection Chesapeake has maintained with many of its graduates.
That sense of generational connection may be one of the school’s most defining characteristics.
Former principal John Yore (2019-2025) once described Chesapeake as a true “community school,” noting that many parents and even members of the faculty were themselves Chesapeake graduates. That overlap between past and present is particularly visible in Pasadena, where families often remain in the community for decades.
Now, as Chesapeake enters its 50th-anniversary year, another familiar face is leading the school.
Principal Shanna Cahoon took the helm ahead of the 2025-26 school year after previously spending eight years as an assistant principal at Chesapeake. After a year as an assistant principal at Old Mill High School, Cahoon returned to Pasadena to lead the Cougars last year – a homecoming of her own as the school approached one of the biggest milestones in its history. “Chesapeake has the most incredible community of students, teachers, families, and partners I have ever experienced. The strong relationships, dedicated educators, and amazing students create a truly special environment. I feel honored to serve a school where the sense of pride, connection, and commitment to student success is so deeply rooted,” Cahoon said.
Her leadership places Chesapeake at an interesting crossroads: celebrating five decades of tradition while preparing students for a world that would have been almost unimaginable when the school’s first students entered the building in 1976.
The school has not yet publicly released a complete calendar of 50th-anniversary festivities, but the anniversary year provides an opportunity for Chesapeake to recognize alumni, former staff members, longtime traditions and the generations of families that have helped shape the school. Additional anniversary recognitions and events are expected to take shape as the school year unfolds.
And there is plenty to look back on.
Fifty years means thousands upon thousands of Chesapeake graduates.
It means decades of teachers who spent their careers in Pasadena classrooms, coaches who helped young athletes discover what they were capable of, directors who watched nervous students walk onto a stage and administrators who guided the school through changing times.
It means championships won and games lost, packed homecoming stands, first-day jitters, prom photographs, senior traditions, yearbooks filled with handwritten messages and countless walks across a graduation stage.
It means classrooms that once held typewriters now filled with laptops. Research that once required a trip to the library can now happen in seconds. Students who attended Chesapeake before anyone had heard of the internet now have children – and in some cases grandchildren – attending the same school.
Yet some things about Chesapeake have remained remarkably consistent.
The Cougar still represents the school. The rivalry with Northeast still generates excitement. Generations still gather beneath the Friday night lights. Students still walk into the building as freshmen wondering what the next four years will bring, and they still walk out four years later carrying memories they may not fully appreciate until decades have passed.
Perhaps that is what makes a school’s 50th anniversary meaningful.
Buildings can be renovated. Programs change. Technology evolves. Administrators come and go.
But a school eventually becomes the collection of people who have passed through it.
For half a century, Chesapeake High School has been woven into the story of Pasadena itself – growing alongside the community it was built to serve and becoming a place where generations of local families have learned, competed, performed, celebrated and grown up.
When Chesapeake opened in 1976, it was Pasadena’s new high school, built largely because the community had simply outgrown having only one.
Fifty years later, it is difficult to imagine Pasadena without it.
And as the Cougars celebrate their golden anniversary, Chesapeake High School is not simply marking the age of a building on Mountain Road.
It is celebrating 50 years of people, memories, traditions and Cougar pride – and the generations still to come.
