Spy Exit Interview: Chestertown Town Manager Bill Ingersoll

Capturing decades of public service in a mere ten-minute video is an impossible task., especially when attempting to encapsulate the career of an individual dedicated to fostering community growth, embracing change, and overcoming challenges

For forty-seven years and serving five mayors since 1975, Chestertown Town Manager Bill Ingersoll has overseen the day-to-day operations of the town, managed the town’s budget with the town council, coordinated departments and personnel, implemented policies and initiatives set by the town council, and addressed the needs of the community.

In essence, his efforts have been instrumental in shaping the very fabric of the town we know today.

He’s seen it all—a dramatic reconstruction of impoverished neighborhoods, the creation of Wilmer Park and two others, the waterfront and marina development, and weathering a prolonged recession with limited budgets are but a few examples Ingersoll oversaw during his term as town manager in a complex college community steeped in 18th century American history.

A third-generation Chestertown resident—his grandfather moved to the Quaker Neck area from Chicago in 1911—Ingersoll’s care for and knowledge of the town served him well after a Vietnam-era stint in the Coast Guard and a job for a grant writer opened up the town administration in 1975.

Close to the end of his tenure as Chestertown’s administrative manager, Bill Ingersoll recently talked to the Spy and reflected on his work from the era town hall shared a small building with the police station to the recent building resurgence and economic rebound the town enjoys today.

Sure to be on hand when the new town manager takes the reigns, Ingersoll says “he’s not going anywhere” and will help in any way he can during the transition.

This video is approximately 12 minutes in length.