Frequently Asked Questions

Grant Inquiries

How do I know if I am eligible to submit a letter of inquiry?

The first step is to take the short online eligibility quiz. If you are eligible, you may immediately submit a letter of inquiry.

How can I provide Highland Street Foundation with information about my organization?

We don’t accept unsolicited grant requests. Organizations that have taken the online eligibility quiz and would like to provide the foundation with information can submit a brief letter of inquiry.

Can I submit additional materials with my letter of inquiry?

No, the letter of inquiry should be a brief introduction to your organization and a request for funding. Should the Foundation require additional materials, we’ll contact you directly.

I have submitted the Letter of Inquiry. What next?

After formal review, you will be notified of the status of your inquiry and whether more information about your organization is requested. This process may take up to 12 weeks.

What kinds of organizations do you fund?

Our grants tend to fall under the following areas of interest: education, youth programming and mentoring, housing and homelessness prevention, environment, healthcare and the arts. Please visit our Awarded Grants and Stories of Impact pages for an overview of previous grantees.

What are Highland Street Foundation’s guidelines for making grants?

The grants we make tend to stem from the relationships our trustees have built with our nonprofit partners. Therefore, we don’t seek unsolicited grant proposals, and have no open proposal submission deadlines or pre-established funding limits.

Are your grants restricted to specific geographical regions? 

We primarily fund programs within Massachusetts, but also provide grants to a limited number of organizations outside the state at the request of our trustees. We do not fund organizations based in countries outside the United States.

How often may an organization apply for funding?

We only accept only one letter of inquiry per organization per year.

I have multiple programs for which I would like to submit a letter of inquiry. What do I do?

We request that you choose just one program within your organization to submit information on or, instead, submit a letter of inquiry requesting general operating support.

How can our organization apply for Community Impact Consultants?

Please check the Community Impact Consultants page for more information on this program and the application submission details and deadlines.

Submitting a Proposal

How can I submit my proposal?

We accept proposals online (by invitation only). Invited applicants may enter their invitation code here and begin the proposal submission process.

Can I submit additional materials with my Grant Proposal?

Yes, you can upload additional documents directly to Cybergrants as part of your proposal submission. If you would like to provide additional documents after your proposal has been submitted, please contact

Can I check on the status of grant proposals online? 

The Foundation will contact you directly to inform you of any updates to the status of your proposal.

The person who previously submitted a proposal at my organization is no longer here. What do I do?

Please contact and we can set up a new Grantseeker ID. Please include your name, e-mail address, and a temporary password in your request e-mail.

I was not able to submit my proposal. Who can I contact?

Please contact with any questions regarding issues with submitting your proposal online.

Existing Grantees

Can I submit reports online? 

Grant recipients required to submit an annual impact report (aka progress report or final report) will receive an email reminder when the submission period begins. They may then login to their account to submit the report.

I received a grant through Highland Street Foundation’s Youth Philanthropy Program and would like to apply for another grant. What do I do?

If you have received a grant from Highland Street through our Youth Philanthropy Program and would like to apply for another grant, please submit a letter of inquiry. For more information on this process, please visit our Grant Inquiries page.

How can I contact a Highland Street Foundation Trustee?

Please send all correspondence to the Highland Street Foundation offices addressed to the trustee you would like to contact.