Scholarship Winners
| Year | Chester Alumni Association Scholarship | Ruth Parkin Carroll Memorial Scholarship | Descendant Scholarship | Vocational/Technical School Scholarship | Chester Alumni Association Scholarship Sponsored by Main Street Pizza |
| 2020 |
Liam Fentazi |
Julia Upeslacis |
Emily Ocasio |
Nicholas Colban |
|
| 2021 |
Ekhine
Avalos Colin |
Joshua Torres |
No Applicants | Not Available for this year | |
| 2022 | Ryan Scalerno | Alyssa Kreischer | Jacob Gecht | Not Available for this year | |
| 2023 | Autumn Tyler | Alia Mahmood-Ul-Haq | Tyler Csernai | Not Available for this year | Adriana Bonilla |
| 2024 |