As many of you know, the Colonial Challenge Cup has been raising funds for Education through the holding of an annual sailing regatta on the Chesapeake Bay, Maryland, USA since 1986. But for a brief hiatus in the mid 2000's, the regatta has been the focus for old friends, family members and guests to compete in a friendly atmosphere, for the most part, over three days, rain or shine, in the waters off St. Michael's.  


In 2006, we added the CCC Track Day to the calendar.  The polar opposite to the regal sport of sailing, it provided motoring enthusiasts and some sailors, with the chance to experience the fun and exhilaration of learning how to drive their everyday car in a controlled environment on a road course. This event was also 'rested' after the Great Depression, but 2017 saw its return with gusto.


Our support of the Annapolis Trust has never wavered, even during the down years. To date we have raised over $200,000 which has been used to provide financial support to the seventy three students who have graduated from college, community college or technical school. Our scholars, who are mainly first in family students, have shown their true dexterity and desire to succeed at school and thereafter despite some of the challenges that they have faced in their lives. For more about the Annapolis Trust, please visit the web site


Hear it from the students:

“The Annapolis & Anne Arundel Scholarship Trust was an aspiration for me to be a first-generation college graduate and I am very much appreciative of the financial support that it provided to my education.”


- Tierra Snowden, Analyst for National Center of Children and Families and BS, Biology, UMES 2006


“I would like to first thank the Colonial Challenge Cup for sponsoring me with the Annapolis and Anne Arundel Trust Scholarship. My first semester is going well, I am prospering through introduction to biology and introduction to psychology”

- Terrence Agbaw, Masters in Cyber Technology, Towson University 2018

© 2020 by Colonial Challenge Cup.  The Colonial Challenge Cup is a registered tax-exempt non-profit under section 501(c)(3) of the Internal Revenue Code.