Since 2000, the Middle School was completely rebuilt from an aging stable to a modern three level classroom and performance area complex.

Responsible for growing the school from one without a unified grading system to a nationally accredited institution, Gregory served for 29 years.

Portledge offers many sports that are taught to students between fifth and twelfth grades, a number of which are not found in most public schools.

In its past years, Portledge has been successful in sports competing in championship competition such as the International Private and Parochial Schools Athletic League.

Former New York Islanders goaltender and NHL first overall pick Rick DiPietro is the current head coach of the Boys' Hockey team.