After four successful years of service and playing a key role in revitalizing the Main Street Chestertown Program, Kay MacIntosh, MSC ED, is retiring this June. The Board of Directors of Main Street Historic Chestertown is seeking a highly organized, detail-oriented, self-starting individual for its full-time Executive Director position.

The Executive Director of MSC is responsible for the management, coordination, administration, documentation, and implementation of MSC’s revitalization program. The day-to-day operations include but are not limited to: managing the organization’s grant and fundraising program; coordinating the activity of all MSC committees, volunteers and work teams; working collaboratively with MSC District property and business owners, the network of Maryland Main Street programs, and local government and partner agencies; representing and advocating for MSC at public forums; handling or supervising the design of marketing campaigns; and planning and coordinating community and fundraising events.

The ideal candidate is a proven leader experienced in business development. Education and prior experience in economic development or non-profit administration are highly desirable. The Executive Director must be able to communicate and work well with others, including existing and new businesses, other local partner organizations, and elected officials, and have excellent technology and social media skills. For the complete job posting, please visit

Candidates should express their interest no later than April 15, 2021 by submitting a cover letter, resume and references to

Main Street Historic Chestertown (MSC) is a 501(c)(3) non-profit corporation, and a designated Main Street Maryland program, with a mission to foster an inviting, diverse and prosperous downtown Chestertown.