Conceived and founded by Konrad “Chip” Kruger, the former Co-Head of Greenwich Capital, Waterside School opened its doors on September 10, 2001 with a kindergarten and first grade, five teachers, 27 students, modest means and an ambition anything but. The School was founded on the belief that the one thing owed to every child is the opportunity for a proper education and was purposefully designed to offer an alternative to the region’s public-school experience while providing for its graduates a path to the area’s finest and most competitive independent schools.

The School weathered a first decade of stubborn struggle and was rewarded with the successful completion of the $24mm Campaign for Waterside and the construction of the current facility in the South End of Stamford in 2011. Along that journey, the School was formally accredited by the Connecticut Association of Independent Schools (CAIS) in 2008 and, throughout, it has honored its founding mission – to attract and inspire students of academic promise and families deeply invested in their children’s success, and to instill in its students a belief in their own worth, to cultivate in each a commitment to excellence and to ensure the fullest development of every child’s character.

The School’s second decade has been one of unmeasured success with its graduates earning admission and scholarships to the area’s strongest schools; attending the finest colleges and universities; and, proving the wisdom of the investment made in each, pursuing lives of genuine and generous success. In result, the most American of ideals – the belief that every child should have the opportunity to become anything – has been made so very real.

Glowingly re-accredited by CAIS in 2018, the School’s immediate future could not be brighter. Making it so – a faculty of talent, passion and commitment; a parent body fully invested and engaged; a school community strong and true; a reputation for proven excellence; a base of support generous and loyal; the financial resources necessary to support the enterprise; and, in 2020, the acquisition of real estate contiguous to the School providing opportunity and optionality for future growth. The School’s third decade will mirror the success of the two preceding and will continue to allow the School to set standard and to provide life-changing opportunities for those able and deserving.

Belief in Self Worth

The belief that the true measure of a child is not to be found in what they are given but rather in what they have worked to overcome; the belief that talent, hard work and character not circumstance should ultimately determine every child’s destiny; and the welcome lesson that the Dream, one uniquely American, is alive and well, here and now, with us and with ours.


As Waterside families are asked to pay only as they can afford, tuition revenue accounts for only 7% of the School’s operating revenue. All other funding comes from generous individuals, foundations and corporations.

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