| Beagary Charitable Tr | | Brooklyn, CT | Local | 4 | 2024 | $50,000 |
| Marthas Vineyard Community Foundation Inc | | West Tisbury, MA | Local | 4 | 2024 | $40,500 |
| West Chop Community Fund Inc | | Vineyard Hvn, MA | Local | 1 | 2024 | $35,000 |
| Couch Family Foundation | | Hanover, NH | National | 3 | 2024 | $27,500 |
| Peter and Anna Kolchinsky Foundation | | Portsmouth, NH | Local | 1 | 2024 | $20,000 |
| Giordano Foundation Inc | | Vero Beach, FL | Local | 2 | 2024 | $7,550 |
| Doug Flutie Jr Foundation for Autism Inc | | Newton, MA | Local | 1 | 2024 | $7,500 |
| Slough Farm Foundation | | Edgartown, MA | Local | 1 | 2024 | $7,500 |
| James Held & Kenn Karakul Charitable Foundation Inc | | Palm Beach, FL | Local | 1 | 2024 | $5,000 |
| If Hummingbird Foundation Inc | | Greenwich, CT | Local | 4 | 2024 | $4,950 |
| Jmg Family Foundation | | Wilmington, DE | Local | 4 | 2024 | $3,650 |
| Alden Charitable Foundation Inc | | Guilford, CT | National | 1 | 2023 | $7,800 |
| Cutler-Stephens Foundation | | Charlestown, MA | Local | 6 | 2023 | $4,100 |
| Hawkswaney Foundation | | Chilmark, MA | Local | 2 | 2023 | $2,000 |
| Saramar Charitable Fund Tr | | Philadelphia, PA | Local | 5 | 2023 | $1,850 |
| Marthas Vineyard Bank Charitable Foundation Inc | | Edgartown, MA | Local | 1 | 2023 | $1,250 |
| James C and Norma I Smith Foundation | | Dallas, TX | National | 6 | 2022 | $6,000 |
| Rockland Trust Foundation Inc | | Rockland, MA | Local | 2 | 2022 | $5,000 |
| Cape Cod 5 Foundation Inc | | Hyannis, MA | Local | 1 | 2021 | $1,000 |
| Rockinghorse Trail Foundation | | Boston, MA | Local | 1 | 2021 | $500 |
| Robert Day Foundation | | Los Angeles, CA | Local | 1 | 2020 | $5,000 |
| Peter & Elizabeth C Tower Foundation Tr | | Getzville, NY | Local | 1 | 2020 | $5,000 |
| Edward H Benenson Foundation Inc | | New York, NY | National | 2 | 2020 | $2,000 |
| Sibbri Foundation | | Vineyard Hvn, MA | Local | 1 | 2020 | $1,000 |
| Richard and Bette Saltzman Foundation | | New York, NY | Local | 2 | 2020 | $1,000 |
| Wianno Sailing Foundation Inc | | East Sandwich, MA | Local | 1 | 2020 | $500 |
| Salvatore Giordano Foundation | | | — | 3 | 2019 | $15,000 |
| Permanent Endowment Fund for Martha's Vineyard | | | — | 1 | 2018 | $10,500 |
| Hoerle Foundation | | New York, NY | Local | 1 | 2018 | $10,000 |
| Robert Dudley Harrington Jr Charitable Foundation | | New York, NY | National | 1 | 2018 | $5,000 |
| Howell Family Foundation Under Declaration of Tr 06171998 | | Boston, MA | Local | 1 | 2018 | $1,500 |