Main Street Historic Chestertown is inviting civic-minded community members to apply for open seats on its Board of Directors. As a 501(c)(3) non-profit organization, Main Street Chestertown is dedicated to preserving, enhancing, and promoting historic downtown Chestertown. The organization guides its work through four core goals, focusing on driving business expansion and diversification, supporting residential and downtown growth, fostering cultural and recreational vitality, and enriching local streetscapes and the waterfront.

Main Street Chestertown continues to build momentum across the downtown district. Recent accomplishments include awarding more than $100,000 in grants, overseeing an increase in visitors to the Visitor's Center, launching the Down on Main Street campaign with The Chestertown Spy, enhancing partnerships and resource sharing with our downtown organizations, and putting on its annual signature event, Dickens of a Christmas, which draws visitors from across the region to experience one of a kind holiday magic in the historic town. This year’s event is happening Dec. 4 and 5. 

Looking ahead, the organization is focused on supporting key revitalization efforts, including commercial property repairs, enhancements to the town waterfront, and historic preservation of our downtown residences. Programmatic focuses include growing and expanding tourism and new business attraction efforts, and bolstering our existing businesses. 

To support this ongoing work and bring additional expertise and capacity to its board and committee structure, Main Street Chestertown is expanding its board from its current eight members to a target of 10 to 11 members. While all interested community members are encouraged to apply, a recent board evaluation identified specific priority areas for this recruitment cycle. The board is particularly interested in applicants with experience in law and contracts, fundraising and donor cultivation, tourism and hospitality, retail, food and experiential businesses, and nonprofit management.

Main Street Chestertown also believes its leadership is strongest when it brings together a broad range of perspectives and experiences. The organization welcomes candidates of different ages, backgrounds, lived experiences, professions, and connections to the community as it works to broaden representation on the board.

“Chestertown is an incredibly special place - it’s the history and beauty of the town, of course, but it’s also the creativity and sense of community that you find here. We’re looking for board members who recognize what we have, are excited about what’s possible, and want to be part of helping it grow,” said Board President Rebecca Clark. “That means bringing new skills and perspectives, but also a genuine willingness to get involved and contribute. We have so much worth preserving, and want to make sure we’re also making room for new ideas, new voices, and the next generation of people who will care for this community.”

Those interested in joining the board are encouraged to apply this month. The application window opens Wednesday, November 4, 2026, and closes Tuesday, December 1, 2026, at 5:00 PM. The Nominating Committee will review applications and conduct candidate interviews throughout December, with slated candidates presented in early January ahead of a full board vote and new member orientation in late January or early February 2027.

Interested candidates can apply by submitting a resume and a brief statement of interest detailing why they wish to serve and what perspectives they bring to Main Street Chestertown. Submissions can be emailed directly to manager@mainstreetchestertown.org. Typically, the board meets 10 months a year. Community members with questions regarding board service expectations are encouraged to reach out via email for more information. 

Main Street Chestertown is dedicated to preserving, enhancing, and promoting historic downtown Chestertown. Through community collaboration, business advocacy, regional tourism promotion, and structural enhancement programs, the organization works to enhance the quality of life for residents and visitors alike.