New Chestertown Main Street Executive Director Nina Fleegle

The Board of Directors of Main Street Historic Chestertown is pleased to announce that Nina Fleegle will join the Main Street program on July 1 as its new executive director.

Fleegle brings a wealth of experience in nonprofit management, volunteering and event-planning to the job. Most recently she has served her alma mater, Washington College, as Associate Director in the Office of Advancement and Constituent Relations. She earlier worked for the College’s Career Development Center and Office of Alumni Relations and Annual Giving. Other career experience includes stints at Holy Trinity School in Washington, D.C., and AmeriCorps, and a six-month teaching job with the Peace Corps in the African Republic of Cape Verde. She also is a certified event planner and owner of Chester River Events.

As a volunteer, Fleegle serves on the Board of United Way of Kent County and on the Kent Family Center Advisory Board and chairs the Young Professionals of Kent County.

Fleegle replaces Kay MacIntosh, who revived the nonprofit and administered it for five years before retiring from her position as Chestertown’s Economic Development Director earlier this month. “We appreciate all Kay did to re-establish our Main Street nonprofit and develop it into an effective and respected force for economic development downtown,” said Board President Paul Heckles in announcing the new hire. “We are thrilled to welcome Nina with her skill set, experience and community connections.  She’s the perfect person to keep us moving forward with current programs and to help us launch some major new initiatives.”

“I love Chestertown and am thrilled to have this opportunity to make a difference through Main Street,” said Fleegle. “There’s so much potential for building on the Town’s strengths and making improvements that will draw more businesses, residents and visitors to downtown.”

Part of a national network established by the National Trust for Historic Preservation, Main Street Historic Chestertown is a 501(c)3 whose mission is to foster an inviting, diverse and prosperous downtown, where people of all ages and backgrounds are drawn to live and work. Following the national model for revitalization of historic commercial districts, MSHC focuses on enhancing the streetscape, supporting local businesses, creating events and activities that draw people downtown, and promoting Chestertown as a destination for shopping, dining and entertainment. For more information visit and