The Cummings Foundation's 2026 $30 Million Cycle: 150 Multi-Year Grants, a September 17 LOI, and a Volunteer-Driven Selection Process That Rewards Local Specificity

When the Greater Milwaukee Foundation announced earlier this month that it had distributed $96.9 million in grants during its most recent fiscal year — the largest annual figure in its 110-year history — the headline reinforced a story that has been quietly building across American philanthropy: as federal grantmaking faces a politically driven pre-issuance review framework under the proposed 2 CFR 200 rewrite, private and community foundations are stepping more visibly into the funding gaps. Few foundations have done so with the specific structural commitments that Cummings Foundation, the Woburn, Massachusetts–based grantmaker founded by Bill and Joyce Cummings, has built around its $30 Million Grant Program.

That program's 2026 cycle is now open. Letters of inquiry will be accepted via Cummings' online portal beginning July 15, 2026 and through 5:00 p.m. on Wednesday, September 17, 2026. The cycle will fund 150 nonprofits across greater Boston through a combination of three-year and ten-year multi-year grants, with annual installments ranging from $10,000 to $100,000. The structural choices baked into the program — multi-year, operating-support-friendly, volunteer-evaluated, and tightly geographically restricted — make it one of the most distinctive grant opportunities of its size in the country, and they reward a very specific kind of applicant.

The program's design and why it matters

Cummings Foundation has been running the $30 Million Grant Program in its current form since 2020. The architecture has hardened with each cycle, and the 2026 round will follow the same template that produced the foundation's most recent class of grantees:

• 150 total grants will be awarded.
• 125 of the 150 will be three-year grants, with award value distributed in equal annual installments.
• 25 of the 150 will be ten-year grants, available only to prior Cummings grantees who meet additional readiness criteria and are selected for committee presentations during the spring "Presentation Days."
• Annual installments range from $10,000 to $100,000, in round-number increments, and remain constant across the grant period.
• Grants of $25,000 or less per year can be applied for via a short-form application that defaults to general operating support and does not require a project budget.
• Grants above $25,000 per year require the comprehensive application and a project or operating budget.

The choice to anchor the program in multi-year, operating-support-friendly grants is not incidental. It reflects a long-running conviction within the Cummings family that nonprofits perform better when they are not forced to repackage operating work as project work to attract restricted funding. The 2026 cycle continues that posture, and applicants who structure their LOI around stable, predictable operating needs — rather than a discrete project that happens to align with the foundation's interests — typically perform better.

The ten-year grant track is the most distinctive feature of the program and the one applicants most often misunderstand. The ten-year designations are not selected at the LOI stage. They are applied retroactively, after the initial 150 winners have been chosen, to a subset of grantees who (a) are prior Cummings recipients, (b) requested more than $25,000 per year, and (c) responded to an application question about organizational readiness for long-term funding. The candidates are then reviewed against impact reports and volunteer site-visit reports, and the top set are invited for committee presentations in May. The implication for first-time applicants is direct: there is no path to a ten-year grant in cycle one. The path to a ten-year grant runs through a successful three-year grant in a prior cycle, a strong impact report, and an excellent site visit.

Geographic eligibility is narrow and strictly enforced

Cummings Foundation is explicitly a regional funder. To be eligible, applicants must be headquartered and provide the majority of their services in one of the following Massachusetts counties:

• Essex County
• Middlesex County
• Suffolk County
• Norfolk County, but only in the specific communities of Brookline, Dedham, Milton, Needham, Quincy, and Wellesley

Organizations that also serve communities outside Massachusetts are eligible only in one narrow exception: Merrimack Valley nonprofits serving Southern New Hampshire. Beyond that, an organization that maintains offices or provides services outside Massachusetts is ineligible, even if its headquarters falls inside the geographic boundary. This is policed strictly. Cummings Foundation does not view itself as a national funder, and applications that read as national or regional in scope are filtered out at the LOI review stage.

The geographic restriction is one of the program's strongest features, not a limitation. It means that the foundation's volunteers are evaluating applications from organizations they can plausibly know personally, and that the ~$1 billion of cumulative grantmaking Cummings has now done has concentrated in a single regional ecosystem. Greater Boston nonprofits effectively have a major institutional funder whose annual deployment is comparable to the largest community foundations in the region.

Organizational eligibility: what disqualifies an applicant

The program is open to 501(c)(3) public charities meeting the geographic test, but Cummings Foundation applies several additional filters that disqualify a meaningful share of would-be applicants:

• Endowments, private foundations, and medical research entities are not eligible. Cummings views these as funded through different channels and not the constituency the $30 million program is designed to serve.
• Religious organizations are not eligible for funding of religious activities. (Faith-based organizations doing secular service work can apply, but the line is policed during review.)
• Political and lobbying organizations are excluded.
• Newly formed nonprofits are generally not competitive, although the foundation does not publish a hard tenure threshold. In practice, organizations with fewer than three full audited fiscal years rarely advance past the LOI stage.
• Very large, endowment-backed organizations are de-prioritized. The foundation is explicit that it is not seeking to add marginal capital to institutions that already have substantial reserves.
• Primary and secondary schools that charge significant tuition are excluded, with the exception of public schools in the 11 communities where Cummings operates commercial real estate properties.
• Municipalities are generally excluded, with the same narrow public-school exception.
• Local affiliate offices of larger national organizations are excluded unless they are separately incorporated with their own EIN.
• Organizations that "infringe on civil liberties or personal freedoms" or that "treat people unfairly" based on protected characteristics are excluded — a policy the foundation has applied consistently across cycles.

The program is also explicit about funding focus. The 2026 cycle, like recent prior cycles, prioritizes human services, fairness and justice, education, healthcare, and environmental initiatives. Athletics, arts and culture, land preservation, and animal welfare are not currently considered. Arts organizations in particular often miss this — the foundation has supported arts work in prior years but has narrowed its scope, and an arts-led LOI in the current cycle will not advance regardless of quality.

The volunteer evaluation process: why it changes how to write the LOI

Most foundation grant programs are evaluated by program officers — full-time staff with subject-matter expertise in the funder's focus areas. Cummings Foundation, almost uniquely at this scale, does not work that way. More than two-thirds of the 150 awards each year are determined by volunteers — roughly 100 community members serving on four successive committees, each of which narrows the pool from LOI through final selection.

The implications for application strategy are significant.

First, the LOI is read by volunteers with varied (and sometimes shallow) familiarity with the specific issue area. Technical jargon, sector-specific acronyms, and assumed background knowledge all hurt. The LOIs that advance are written in plain language, with concrete examples, and with a clear theory of how the organization's work changes outcomes for the people it serves. The most successful applicants treat the LOI as a story told to a thoughtful neighbor, not as a technical brief to a foundation officer.

Second, volunteers respond strongly to local specificity. An LOI that names neighborhoods, schools, partner organizations, and (where appropriate) individual clients or program participants reads more credibly than one written in generalities about "underserved communities" or "vulnerable populations." Cummings volunteers tend to live in the communities the foundation funds. They notice when an applicant's description of a problem matches their own observation of it.

Third, the committee structure means that an LOI that survives the first round will be re-read by different volunteers in subsequent rounds. Consistency between the LOI, the full application (for those invited), and the budget matters. Applications that pass the LOI screen but then introduce new program directions, new geographic scopes, or new funding asks in the full application stage tend to lose in committee.

The timeline applicants should plan around

• July 15, 2026: LOI portal opens.
• September 17, 2026, 5:00 p.m.: LOI deadline. The portal closes at exactly 5 p.m. and does not accept late submissions.
• Week of November 3: Invitations to submit full applications are sent to a subset of LOI submitters.
• January 14, 2027, 5:00 p.m.: Full applications due.
• Week of May 11, 2027: "Presentation Days" for ten-year grant candidates.
• June 1, 2027: Grant decisions announced.
• June 25, 2027: Grant winner celebration event.

The first installment of three-year grants is typically disbursed within weeks of the June announcement, with subsequent installments arriving on the same calendar in each of the following two years.

How this fits the broader 2026 funding landscape

The Cummings $30 million cycle lands at an unusually favorable moment for nonprofits that fit its profile. Federal grantmaking is in the middle of a significant restructuring — the OMB rewrite of 2 CFR 200 and the HHS QSMO migration being the two most consequential pieces. State and local government funding is under similar pressure in many jurisdictions. Private and community foundation capital has not grown to fully offset the federal contraction, but the foundations that have committed to multi-year operating support have become disproportionately important to the field's stability.

Cummings is one of the largest of those foundations on a per-grant basis, and it operates entirely outside the federal cycle. The grants are unrestricted-friendly, multi-year, and disbursed on a predictable annual cadence. For a Greater Boston nonprofit that fits the eligibility criteria, the $30 million cycle is not a marginal opportunity. For organizations with annual budgets under $5 million, a successful three-year award at $50,000–$100,000 per year can represent a meaningful share of unrestricted operating capital — the kind of capital that allows organizations to plan, hire, and invest without the year-to-year scramble.

The application is comparatively light by the standards of foundation grantmaking — a short LOI, with the comprehensive application only required from invited finalists. The cost of applying is low; the cost of failing to apply, for an organization that fits the program, is the loss of one of the most accessible large-scale unrestricted funding opportunities in the region.

For eligible Greater Boston nonprofits, the period between now and September 17 is the relevant planning window. Organizations that have not yet built a relationship with Cummings should use the next several weeks to attend one of the foundation's information sessions, read recent grantee impact reports (publicly available on the Cummings site), and structure their LOI around a clear local theory of change rather than a generic problem statement. The committee process rewards specificity, and specificity takes time to write.