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. If you have any questions, please check out our Frequently Asked Questions page. If the answer to your question cannot be found there, feel free to contact us.

Current Opportunities

  • Theme: Leadership • Community Impact
    Eligibility: Boston high school juniors and seniors
    Awards: Two winners — $1,000 each
    Due Date:     January 31, 2026
    Decision Date: February 16, 2026

    Scholarship Prompt & Required Uploads: 

    1) Submit an essay of 500-700 words that responds to the following prompt: Describe a moment you stepped up when no one asked you to.

  • Theme: Perseverance • Resilience  • Academic Commitment
    Eligibility:

    • Massachusetts charter school students 

    • GPA 2.7+ or clear evidence of academic growth

    Awards: Three Awardees - $1,500 each
    Due Date: February 28, 2026
    Decision Date: March 16, 2026

    Scholarship Prompt & Required Uploads: 

    1) Submit an essay of 500-750 words that responds to the following prompt: Describe a challenge that tested your grit. How did you push through, and what achievement came from that resilience?

    2) Submit a transcript to demonstrate either at least a 2.7 GPA or clear evidence of academic growth; and

    3) One recommendation attesting to your academic achievement and/or growth.

  • Theme: Black History • Arts & Creativity
    Eligibility:

    • High school or college students

    • Living in Boston or from Boston

    • Individual submissions only

    Awards:

    • 1st Place - $2,000

    • 2nd Place - $1,500

    • 3rd Place - $1,000

    • Honorable Mentions (2x) - $500

    Due Date: February 13, 2026
    Decision Date: February 26, 2026

    Scholarship Prompt & Required Uploads: 

    1) Submit one (1) original creative work in one format:

    • Essay

    • Poem or spoken word (PDF or MP4, 3 minutes or less)

    • Visual art (drawing, painting, sculpture, or photography – JPEG/PNG + brief description)

    • Digital art, animation, or short film (MP4 or unlisted link, 3 minutes or less)

    2) Submit an Artist Statement (150–200 words) that answers the following questions:

    • What inspired this piece?

    • How does the work honor or reflect Black Boston’s history, culture, or impact?

    NOTE: Selected works may be featured (with permission) in Foundation communications.

Apply Now!