Time to Celebrate!

    • HMC Class Agents 2019
    • HMC Drew 2019
The Headmaster’s Challenge runs throughout the month of February and allows Millbrook alumni to participate in a friendly competition that supports their alma mater. For the 2019 Headmaster's Challenge, alumni classes will compete within their decade for the highest percent participation in the Annual Fund.


The 2019 Headmaster's Challenge is ramping up.  Check back regularly for class standings and updates.  If you would like to celebrate the challenge with your classmates, please join us at the event in Boston.  Click the link to the right to register.  There will be a follow up Headmaster's Challenge event in NYC on April 3rd, so make sure you save the date!

2019 Headmaster's Challenge Current Standings

2018 Headmaster's Challenge Results

  • Class of 1942 with 100% participation

  • Class of 1955 with 70% participation

  • Class of 1960 with 61% participation

  • Class of 1978 with 30% participation

  • Class of 1988 with 43% participation

  • Class of 1997 with 84% participation

  • Class of 2003 with 82% participation

  • Class of 2013 with 68% participation