| Date | Name | Symbol | Type | Security | Shares | Price | Value | Ownership | Reported |
| 06/15/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 25 | $32.87 | $821.8 | | 06/15/2023 |
| 03/15/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 17 | $49.63 | $843.7 | | 03/15/2023 |
| 03/10/2023 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Common Stock | 4.9k | $0.00 | $0 | | 03/10/2023 |
| 12/19/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Purchase | Common Stock | 200 | $47.10 | $9.4k | | 12/19/2022 |
| 12/19/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Purchase | Common Stock | 100 | $47.10 | $4.7k | By IRA | 12/19/2022 |
| 12/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 18 | $46.93 | $844.7 | | 12/15/2022 |
| 09/21/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Payment of Exercise | Common Stock | 420 | $39.30 | $16.5k | | 09/21/2022 |
| 09/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 18 | $38.95 | $701.1 | | 09/15/2022 |
| 08/03/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Purchase | Common Stock | 250 | $32.75 | $8.2k | | 08/03/2022 |
| 06/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 19.51 | $36.43 | $710.7 | | 06/15/2022 |
| 04/29/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Purchase | Common Stock | 200 | $39.45 | $7.9k | By IRA | 04/29/2022 |
| 04/29/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Purchase | Common Stock | 400 | $39.45 | $15.8k | | 04/29/2022 |
| 03/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Phantom Stock | 17.35 | $40.78 | $707.4 | | 03/15/2022 |
| 03/09/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Gift | Common Stock | 30 | $0.00 | $0 | | 04/29/2022 |
| 02/18/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Common Stock | 3.2k | $0.00 | $0 | | 02/18/2022 |
| 02/15/2022 | Orange County Bancorp, Inc. /DE/ | OBT | Payment of Exercise | Common Stock | 1.4k | $41.00 | $57.2k | | 02/15/2022 |
| 09/21/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Grant | Common Stock | 3.5k | $0.00 | $0 | | 09/21/2021 |
| 08/05/2021 | Orange County Bancorp, Inc. /DE/ | OBT | Purchase | Common Stock | 1.5k | $33.50 | $50.2k | | 08/05/2021 |
| 03/06/2014 | HUDSON VALLEY HOLDING CORP | HVB | Payment of Exercise | Common Stock | 111 | $19.53 | $2.2k | | 03/06/2014 |
| 02/20/2014 | HUDSON VALLEY HOLDING CORP | HVB | Grant | Common Stock | 1.9k | $0.00 | $0 | | 02/20/2014 |
| 12/09/2013 | HUDSON VALLEY HOLDING CORP | HVB | Payment of Exercise | Common Stock | 1.1k | $20.26 | $22.5k | | 12/09/2013 |