| 1.   | I                have reviewed this report on Form 10-Q of Smithtown Bancorp                Inc.; |
|----------------|---------------------------------------------------------------------------------------------------|

| 2.   | Based                on my knowledge, this report does not contain any untrue statement                of a                material fact or omit to state a material fact necessary to make                the                statements made, in light of the circumstances under which such statements                were made, not misleading with respect to the period covered by this                report; |
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| 3.   | Based                on my knowledge, the financial statements, and other financial information                included in this report, fairly present in all material respects                the                financial condition, results of operations and cash flows of the                registrant as of, and for, the periods presented in this                report; |
|----------------|-----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|

| 4.   | The                registrant's other certifying officer and I are responsible for                establishing and maintaining disclosure controls and procedures (as                defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) and internal                control over financial reporting (as defined in Exchange Act Rules                13a-15(f) and 15d-15(f))                for the registrant and have: |
|----------------|--------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|

| a.   | designed                such disclosure controls and procedures, or caused such disclosure                controls and procedures to be designed under our supervision, to                ensure                that material information relating to the registrant, including its                consolidated subsidiaries, is made known to us by others within those                entities, particularly during the period in which this report is                being                prepared; |
|----------------|--------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|

| b.   | designed                such internal control over financial reporting, or caused such internal                control over financial reporting to be designed under our supervision,                to                provide reasonable assurance regarding the reliability of financial                reporting and the preparation of financial statements for external                purposes in accordance with generally accepted accounting                principles; |
|----------------|----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|

| c.   | evaluated                the effectiveness of the registrant's disclosure controls and procedures                and presented in this report our conclusions about the effectiveness                of                the disclosure controls and procedures, as of the end of the period                covered by this report based on such evaluations;                and |
|----------------|--------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|

| d.   | disclosed                in this report any change in the registrant’s internal controls over                financial reporting that occurred during the registrant’s                most recent fiscal                quarter (the                registrant’s fourth fiscal quarter in the case of an annual                report)that                has materially affected, or is reasonably likely to materially                affect,                the registrant’s internal controls over financial reporting. |
|----------------|-----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|

| 5.   | The                registrant's other certifying officer and I have disclosed, based                on our                most recent evaluation of internal controls over financial reporting,                to                the registrant's auditors and the audit committee of registrant's                Board of                Directors                (or persons peforming the equivalent functions): |
|----------------|---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|

| a.   | all                significant deficiencies and material weaknesses in the design or                operation of internal controls over financial reporting which are                reasonably likely to adversely affect the registrant's ability to                record,                process, summarize and report financial information;                and |
|----------------|----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|

|                             b. | any                    fraud, whether or not material, that involves management or other                    employees who have a significant role in the registrant's internal                    controls over financial reporting. |
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|                                                      |                                                  |                                 |
|-----------------------------------------------------------|-------------------------------------------------------|--------------------------------------|
| Dated:                  November 8,                  2007 |                                                       | /s/                  Bradley E. Rock |
|                                                      | Bradley                  E. Rock, Chairman, President |
|                                                      | and                  Chief Executive Officer     |

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