South Kent School is home to what some might call a cycling haven offering renown mountain biking program, trails, and hiking trails across 650 acres of gorgeous landscape and completes in the HMBL.

From winding paths through lush forests to scenic routes along historic rail trails, the cycling opportunities at South Kent are as diverse as they are exhilarating. A stones throw from the Appalachian Trail and the recently extended Harlem Valley Rail Trail, South Kent School’s bike trails offer riders a unique blend of natural beauty and rich cultural heritage.

For cycling enthusiasts seeking an adrenaline-fueled adventure, South Kent School boasts an array of thrilling trails that cater to riders of all skill levels. From gentle slopes perfect for leisurely rides to challenging terrain designed to put seasoned cyclists to the test, there’s something for everyone to enjoy. The school’s extensive network of trails meanders through scenic woodlands, offering riders a glimpse of Connecticut’s breathtaking natural beauty at every turn.

One of the highlights of cycling at South Kent School is its proximity to the iconic Appalachian Trail, a legendary footpath that stretches over 2,000 miles from Georgia to Maine. Cyclists can pedal alongside this historic trail, soaking in panoramic views of the rolling hills and verdant valleys that define the Connecticut landscape. With its rugged terrain and awe-inspiring vistas, the Appalachian Trail offers a truly unforgettable biking experience for adventurers seeking a taste of the wild.  See more on All Trails.

In addition to its natural wonders, South Kent School is also home to the newly extended Harlem Valley Rail Trail, a scenic pathway that follows the route of an old railway line through the charming towns of Connecticut’s Litchfield Hills. This recently expanded trail offers cyclists an unparalleled opportunity to explore the region’s rich history and vibrant culture while enjoying a leisurely ride through quaint villages and countryside.  See more Kent Trails.

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Contact our Admissions Team for an in person tour.

We hope you enjoy exploring our beautiful campus, meeting our dedicated faculty, and experiencing firsthand the dynamic student life that defines our school. Should you wish to arrange a personalized visit, please do not hesitate to contact our Admissions Team. They will be more than happy to schedule an in-person tour tailored to your interests and needs.

We would like to extend a special thank you to all the students who have contributed their time and effort to make this tour possible. Your enthusiasm and dedication truly showcase the spirit of South Kent School.

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Once again, welcome, and enjoy your tour!

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South Kent is proud to feature such notable alumni as F.K. Day and Mark B. Thompson have used their engineering and architecture expertise to improve the structural integrity of the world’s buildings and vehicles. William Farish III and Richard H. Lawrence earned their mark on the hallowed Old Building walls as well, thriving in finance and business industries on a global scale.

Another person highlighted in the Old Building includes Shayne Gostisbehere, an NHL player who has dazzled on the ice and in his philanthropic pursuits. Along with athletes, the Old Building possesses South Kent professionals in the arts such as Sarge Pickman, a world-renowned comedian, Charles Reid, the master of watercolor, and James G. Bellows, an editor and publisher of the most famous documents in American history such as Martin Luther King’s “Letters from Birmingham Jail.” Chip Monck also holds a plaque of his own from trailblazing in the music industry and organizing design elements for worldwide events such as the Woodstock Festival and the Olympics.

The Hillside is also proud to share the accolades of two valiant leaders who exhibit their loyalty and patriotism to our country. While John Richardson served as a member of the CIA until 2005, Peter Langenberg’s unwavering commitment to our safety helped him win the Bronze Star, the Purple Heart, and the Prisoner of War Medal. The Old Building’s last two plaques include Walter Strohmeyer, an important figure who has devoted his life to informing American citizens of environmental issues, and James Mercer Garnett Jr., who has displayed impeccable stewardship to South Kent School by innovating for the School’s future while upholding its beautiful traditions.

Other plaques that originally lived in the Old Building will now be scattered across the Hillside campus, serving as a reminder to all students that anything is possible with a positive attitude and a growth mindset. South Kent is excited to exhibit these inspiring journeys, and we look forward to unveiling more stories soon.

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Contact our Admissions Team for an in person tour, learn more about our Open House 2024.

We would like to extend a special thank you to all the students who have contributed their time and effort to make this tour possible. Your enthusiasm and dedication truly showcase the spirit of South Kent School.

Once again, welcome, and we hope to see you on the Hillside!

Tour in Chinese

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Tour in Spanish Coming Soon

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Tour in Portuguese Coming Soon

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Named in honor of beloved faculty members Charlie Whittemore ’39, and his wife Celie Brown Whittemore, this gorgeous trail winds through the Hillside giving those that walk it a feeling of tranquil appreciation for this astonishingly picturesque corner of Connecticut that we call home.

Only four years after graduating from South Kent, Charlie returned to the School as a member of the faculty. Well-loved by students and faculty alike, “Doc” Whittemore was the very spirit of South Kent School. After 45 years of teaching and mentoring boys on the Hillside, Charlie retired. Even after his retirement, his connection to South Kent stayed stron, serving as a Trustee for many years. Celie, too, was a beloved part of the faculty for decades. The class of 1982 regarded her as a superb teacher of French and Biology, and as the gracious person who became synonymous with home. It was on the Hillside that Charlie and Celie met and as they say- the rest is history.

Many alumni fondly recall Charlie and Celie’s after-dinner walks through the woods, strolling at their leisure as the day wound down. We thank the members of the Class of 1965 for stepping up to honor two of the most revered people that walked the Hillside. This beautiful addition to our campus would not have been possible without the help of the Brown and Whittemore families, who guided and stewarded us through the project.

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Named in honor of Samuel Slater Bartlett, whose vision and dedication was fundamental in the founding of South Kent School a century ago. This building stands as a symbol of his lasting impact on the School and our community.

Samuel Bartlett’s commitment to education and character development laid the foundation for South Kent’s mission. As one of South Kent School’s founders, his vision of providing a rigorous and nurturing environment for young men to learn, grow, succeed, and thrive after they’ve left the Hillside, has guided generations of students and faculty.

The legacy of the Bartlett family continued with Sam’s son, George Hodges Bartlett, who followed in his father’s footsteps to become the third Headmaster of our school. Affectionately known as “Mr. B,” George epitomized the values of South Kent- Simplicity of Life, Self-Reliance, and Directness of Purpose.

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Samuel A. Woodward Dormitory is a central point of campus housing, Woodward Dormitory plays a pivotal role in shaping the vibrant community spirit that defines South Kent.  With 42 years of service to South Kent School, Samuel A. Woodward not only brought his expertise as a faculty member teaching history and science, but in his later years he held the title of Business Manager. Joining South Kent just two years out of college, his name became synonymous with one of the greatest that would walk this campus. On his retirement, the class of 1968 dedicated their yearbook to him, noting he leaves behind a heritage of dedication and hard work that pays honor to his will and labor that brought the school into being.

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James R. Garfield ’39 and John Newell Garfield ’43, distinguished alumni of South Kent School, share a notable lineage as the great-grandsons of James A. Garfield, the 20th President of the United States. Their familial connection to such a significant historical figure adds a unique dimension to their legacy and this building. In a generous display commitment to their alma mater, the Garfield Family played a pivotal role in the School’s development by funding the construction of the Garfield dorm. This residence stands as a testament to their dedication, named in honor of their mother, Janet Dodge Garfield. The Garfield dorm not only serves as a physical space for students, but also as a lasting symbol of the family’s enduring support for education and the South Kent School community.

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Jerry Waller, an esteemed alum of South Kent School’s Class of 1935, dedicated nearly four decades of his life to the School. Joining the faculty in 1946 and retiring in 1982, Jerry left an indelible mark on South Kent as an educator, mentor, and coach. As Chairman of the Foreign Language Department, he shared his passion for languages and culture with his students, teaching French with enthusiasm and expertise. Additionally, Jerry’s influence extended to the athletic arena, where he coached hockey and tennis, imparting invaluable lessons of teamwork, perseverance, and sportsmanship to his players.

Nancy Waller was equally integral to the fabric of the South Kent community. Known for her warmth and hospitality, she graciously opened her home to numerous students over the years, creating a sense of family and belonging that extended far beyond the classroom walls. Together, Nancy and Jerry epitomized the spirit of South Kent School, fostering an environment where students could thrive academically, athletically, and personally.

As South Kent School continues to uphold its commitment to excellence in education and character development, the Nancy and Jerry Waller 1935 Memorial Garden will remain a cherished part of the campus landscape. It will serve as a reminder of the values that define the South Kent experience and inspire future generations to carry forth the legacy of Nancy and Jerry Waller—embodying their spirit of kindness, generosity, and love.

Learn more about Nancy & Jerry Waller, and the Dedication of the Waller Garden.

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Named in honor of Elizabeth Bringhurst, the mother of esteemed faculty member Lester “Wuz” Wittenberg, and home to the Maggie Smith Visual Arts Center. Recently renovated to include two new art spaces with ample natural light, these studies serve to unleash our students’ imagination and bring their artistic visions to life. From painting and sculpture to photography and digital media, the new art studios will support a wide range of artistic disciplines, enabling students to explore their interest and develop their skills under the guidance of a supportive and experienced faculty.

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