City on a Hill Scholarships

The City on a Hill Foundation offers a monthly scholarships which feature varying topics and eligibility requirements. While many of our scholarships are reserved specifically for former students of City on a Hill Charter Public School, we also offer opportunities for high school and college students across Massachusetts and nationwide. Before you apply, we recommend that you check out our Frequently Asked Questions. If the answer to your question cannot be found there, feel free to contact us.

Current Opportunities

  • Theme: Alternative Pathways • Persistence
    Eligibility:

    • Current enrollment in a Massachusetts-based alternative pathway (ie. trade school, job development programs, apprenticeship etc)

    • Priority consideration will be given to CoaH alumni

    Awards:

    • 1st Prize - $3,000

    • 2nd Prize - $2,000

    • 3rd Prize - $1,000

    Due Date: June 30, 2026 (Extended from June 14, 2026)
    Decision Date: July 15, 2026 (Originally June 24, 2026)

    Scholarship Prompt & Required Uploads:

    1. An essay (300-500 words) responding to the following prompt: What has taking an alternative pathway to your education taught you?

    2. Evidence of enrollment in an alternative pathway program (including, but not limited to an acceptance letter or a confirmation of attendance from the program on official letterhead).

  • Theme: Civic Engagement • Service
    Eligibility

    • Rising seniors attending any Boston-based 4-year college/university

    • Priority consideration will be given to CoaH alumni

    Awards: Three winners — $5,000 each

    Due Date: July 31, 2026
    Decision Date: August 24, 2026

    Scholarship Prompt & Required Uploads:

    1. An essay (400-600 words) responding to the following prompt: If you could have a conversation with the Freshman version of yourself, what advice would you give them about how to be successful in college/university?

    2. Evidence of enrollment in a 4-year college/university for Fall 2026 (including, but not limited to a current financial aid award or transcript).

  • Theme: Access • Equity • Overcoming Barriers

    • High school or college/university students nationwide

    Awards:

    • Winner — $3,500

    • Runner Up — $2,500

    • Honorable Mention — $1,500

    Due Date: August 31, 2026
    Decision Date: September 15, 2026

    Scholarship Prompt & Required Uploads:

    1. An essay (300-500 words) responding to the following prompt: “Describe a barrier you’ve faced and the creative solution you used to overcome it.”

    2. Evidence of enrollment in an US high school for Fall 2026 (including, but not limited to a current financial aid award or transcript).

Apply Now!

Frequently Asked Questions

  • The City on a Hill Foundation offers a monthly scholarships which feature varying topics and eligibility requirements. While many of our scholarships are reserved specifically for former students of City on a Hill Charter Public School, we also offer opportunities for high school and college students across Massachusetts and nationwide.

  • We post at least one opportunity per month, and they are typically posted at least six (6) weeks before the application deadline.

  • Yes! We encourage you to apply to as many opportunities as you are eligible.

    We ask, however, that you only submit one application per opportunity.

  • Possibly. For the majority of City on a Hill's Monthly Scholarships, we ask that submissions for our opportunities be created specifically for our prompts, as they are often much more specific topics than a personal statement. There may be times, however, when a prompt calls for a portfolio or creative works, and in those cases, a previous used submission can be used for our opportunities. We ask that applicants use their best judgement knowing that their application will be evaluated for adherence to the prompt in addition to its contents.

  • No. City on a Hill does not accept any AI generated or assisted work. If it is suspected that a submission is in part or wholly generated by AI, your application may be marked as ineligible in our system.

  • Our applications are evaluated by a committee of educators from the Boston area, many of whom are previous City on a Hill faculty or Board members. All applications are reviewed by the committee after being anonymized by our applicant system, and committee members are not notified of applicant identities other than those of awardees who are publicly announced.

  • If you are applying to an eligible scholarship as someone who is neither a CoaH alumni nor former faculty/staff, please select “Friend of the Foundation (Other).”

As we carry on the legacy of City on a Hill, we continue to aspire to the value if Public Accountability. One of the ways we do that at the Foundation is publicly posting all of our scholarship awardees so that Friends of the Foundation can see where their support goes in addition to celebrating the awardees and their educational journeys of which we have the honor to have a small role. Click below to check out our awardees!

Our 2025-2026 Awardees

Please note - our awardee pages may not reflect all distributed scholarships, as the Foundation allows awardees to opt out of public posting without penalty to their award or future eligibility for awards.