Windham Foundation

The Windham Foundation is an operating foundation, not a pure grantmaking vehicle — a distinction that shapes everything about how to approach it. Based in Grafton, Vermont, it operates three revenue-generating social enterprises (Grafton Inn, Grafton Village Cheese Company, and Grafton Trails & Outdoor Center) that subsidize both its programs and its external grants. The foundation's reported total giving of $2.67 million (2022) includes the cost of running those enterprises; the actual external grants pool is approximately $330,000–$400,000 annually, distributed across roughly 60–80 organizations. First-time applicants who see the total giving figure and expect large grants will be disappointed — the typical award runs $2,500–$5,000.

The foundation's giving philosophy reflects its operating identity: it funds nonprofits that mirror its own ethos of embedding deeply in Vermont communities and building durable, self-sustaining institutions. Organizations with strong local roots, multi-year track records, and demonstrated community support consistently outperform newer or nationally affiliated applicants. Repeat grantees — St. Johnsbury Academy ($56,000 across two grants), Grace Cottage Foundation ($53,000 across two grants), the Grafton Firemen's Association ($27,676 across four grants) — illustrate that sustained relationships and reliable reporting are rewarded.

Governance is lean and community-oriented. Chairman William Bruett and Vice Chair Alan Yuspeh lead a volunteer board. President/CFO Robert Donald manages operations. Executive Director Dan Lerner oversees the grants program, and Meg Gonzalez serves as the primary applicant contact. The staff knows Vermont's nonprofit landscape personally; a professional, relationship-grounded approach outperforms cold submissions.

There is no formal LOI stage — applications go directly online via grantinterface.com — but the application itself functions as an LOI in scope (3-page narrative maximum, streamlined budget, no extensive attachments). The relationship progression for successful grantees is typically: first award at $2,500–$5,000, demonstrated outcomes, repeat award, deeper project alignment over time, always subject to the three-applications-in-five-years ceiling. For Grafton-area nonprofits, the separate Grafton Fund offers an additional channel.

The Windham Foundation's external grants budget has been remarkably stable across five fiscal years, ranging from $333,106 (2021) to $397,479 (2022), with a five-year average near $370,000 annually. This stability exists against a backdrop of declining total assets — from $51.7 million in 2010 to $18.6 million in 2022 — and falling investment income ($936,000 in 2022 vs. $1.4 million in 2019). The grants-paid line has held steady because the foundation treats its external grantmaking as a protected commitment, absorbing portfolio fluctuations through its operating enterprise revenues.

Grant sizes cluster firmly in the $2,500–$10,000 range. Across 109 grants in the most recent dataset, the median grant is $3,000 and the average is $3,056. The historical grantee database (448 grants, $1.88 million total) shows a slightly higher average of $4,188, inflated by occasional larger awards to long-term partners. The foundation's own guidelines state that grants 'rarely exceed $10,000,' and the maximum in the historical dataset is $12,176. In Fall 2025, 34 organizations shared $137,100 — averaging $4,032 per award — confirming these parameters.

Geographic concentration is extreme: 397 of 448 recorded grants (88.6%) went to Vermont recipients. Outlier awards reached New York (12 grants), New Jersey (9), Florida (7), Massachusetts (5), and smaller numbers elsewhere — likely reflecting organizations with strong Vermont programmatic ties but non-Vermont incorporation.

By program area, the foundation's 2026 themed cycles reveal four roughly equal buckets: (1) economic and workforce development, (2) food/conservation/climate, (3) arts/learning/mentoring/historic preservation, and (4) wellness/housing/senior programs. Historically, education and arts institutions appear most frequently in the grantee list (St. Johnsbury Academy, Shelburne Farms, Vermont Symphony Orchestra, Yellow Barn, Flow of History Inc.), followed by environmental and land conservation organizations (South Hero Land Trust, Preservation Trust of Vermont, Green Mountain Conservancy, Rich Earth Institute), and then human services (Hunger Free Vermont, Meals on Wheels, Community Harvest of Central Vermont).

Per-cycle giving averages approximately $65,000, distributed among 30–40 recipients. This means competition within each themed cycle involves roughly 30–40 funded organizations drawn from what is likely a pool of 100–200 applications.

Windham occupies a distinct niche in this peer set as the only operating foundation, meaning its grantmaking is one expression of a broader place-based mission rather than a stand-alone charitable program. Vermont Community Foundation offers far larger grants (up to $500,000+) with statewide reach but far more competition. Lintilhac and High Meadows are better-capitalized and better-paying but essentially closed to cold applicants. For small Vermont nonprofits seeking $3,000–$10,000 in project or operating support with a streamlined, direct-application process, Windham is the most accessible private foundation entry point in the state. Organizations pursuing Windham should also prospect the Vermont Community Foundation's field-of-interest and component funds, which sometimes overlap thematically and accept applications on similar timelines.

The most consequential recent development at the Windham Foundation is Executive Director Dan Lerner's restructuring of the grants program from quarterly cycles to two themed annual cycles (announced 2024, fully implemented by 2025). Where previously any Vermont-focused nonprofit could apply in any quarter against broad criteria, applicants now compete within thematic pools tied to the Spring (March 15) or Fall (September 15) cycle. Lerner publicly stated the dual goals: helping the foundation identify mission-aligned work within each focus area, and enabling applicants to compete with peer organizations rather than across all sectors simultaneously.

In Fall 2025, 34 Vermont nonprofits received $137,100 under the themes of Preserving and Developing Resilient Communities and Healthy and Vibrant Communities. Recipients included Vermont Works for Women, ARC Rutland Area, Grace Cottage Hospital, Girls on the Run, and Vermont Parks Forever — a cross-section of workforce, disability services, healthcare, youth development, and conservation.

In January 2026, the foundation publicly announced both 2026 cycle themes and deadlines. The Spring 2026 cycle (deadline March 15, 2026 — now passed) focused on economic/workforce development in rural contexts and food/conservation/climate adaptation. The Fall 2026 cycle (deadline September 15, 2026, 5:00 PM) targets community arts, enhanced learning, mentoring, historic preservation, wellness, housing, outdoor activities, health access, and senior programs.

No major leadership transitions or endowment events have been publicly reported beyond this program restructuring. The foundation continues to operate the Grafton Inn, Grafton Village Cheese Company, and Grafton Trails & Outdoor Center as core social enterprises.

Match the cycle theme before anything else. The Windham Foundation evaluates proposals within themed pools — economic/workforce, food/conservation, arts/learning, or wellness/housing/senior. A strong proposal submitted in the wrong cycle will not advance regardless of organizational merit. For Fall 2026 (September 15 deadline), the relevant themes are community arts, enhanced learning, mentoring, historic preservation, wellness, housing, outdoor activities, health access, and senior programs. Do not stretch a proposal to fit; if your work doesn't align, wait for Spring 2027.

Contact Meg Gonzalez at meg.gonzalez@windham-foundation.org (802-843-2215) at least 6 weeks before the deadline to confirm theme fit. This brief exchange is the practical substitute for a formal LOI and begins your relationship with the program officer. Include one paragraph describing your project and explicitly ask whether it aligns with the current cycle.

Secure your 50% match first, then apply. The foundation will not fund more than half of any project. Before drafting the narrative, confirm co-funding — from earned revenue, other grants, or individual donors — totaling at least as much as your Windham request. List every source above $1,000 in your budget. Proposals with speculative or undocumented co-funding routinely fail.

Write the 3-page narrative with surgical precision. Cover three areas: (1) your organization's expertise and track record in the program area, including population served and geographic reach; (2) the specific problem and your solution, with goals, activities, and timeline; (3) how you will measure and report impact, and how the work will continue after the grant period. Use Vermont-specific language — name towns, reference local supply chains or partnerships, demonstrate understanding of rural context.

Submit full board bios. A brief 3-5 sentence bio per board member is required and frequently incomplete in failed applications. Frame bios around professional expertise and community connection, not just titles.

Track your application history. The foundation enforces a one-application-per-12-month-period limit and a three-applications-per-five-year cap. A wasted application slot against the wrong cycle or at the wrong time is difficult to recover from. Organizations already at two applications in five years should treat their next submission as their most carefully prepared.

Highlight collaboration. Partnerships with other Vermont nonprofits are explicitly preferred. Name partners, define roles, and quantify combined reach.