| Date | Name | Symbol | Type | Security | Shares | Price | Value | Ownership | Reported |
| 09/21/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Payment of Exercise | Common Stock | 240 | $44.25 | $10.6k | | 09/21/2023 |
| 08/07/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Sale | Common Stock | 784 | $48.85 | $38.3k | By 401(k) | 08/07/2023 |
| 03/10/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Common Stock | 1.8k | $0.00 | $0 | | 03/10/2023 |
| 11/21/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Sale | Common Stock | 1.5k | $46.50 | $69.8k | By IRA | 11/21/2022 |
| 09/21/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Payment of Exercise | Common Stock | 240 | $39.30 | $9.4k | | 09/21/2022 |
| 09/21/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Payment of Exercise | Common Stock | 240 | $39.30 | $9.4k | | 09/21/2022 |
| 06/29/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Other | Common Stock | 527 | $37.97 | $20k | By 401(k) | 05/04/2022 |
| 05/09/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Other | Common Stock | 404 | $37.11 | $15k | By 401(k) | 05/04/2022 |
| 05/04/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Other | Common Stock | 1.3k | $39.45 | $50k | By 401(k) | 05/04/2022 |
| 02/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Common Stock | 1.7k | $0.00 | $0 | | 02/15/2022 |
| 02/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Payment of Exercise | Common Stock | 553 | $41.00 | $22.7k | | 02/15/2022 |
| 09/21/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Common Stock | 2k | $0.00 | $0 | | 09/21/2021 |
| 08/05/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Purchase | Common Stock | 500 | $33.50 | $16.8k | | 08/05/2021 |