Executive Director

Main Street Historic Chestertown

Help Lead one of Maryland’s Most Lovable Small Towns

Chestertown has the kind of downtown people write about—charming, walkable, and full of familiar faces. Set along the Chester River on Maryland’s Eastern Shore, our historic waterfront town is home to independent businesses, artists, entrepreneurs, Washington College, and neighbors who care deeply about their downtown.

Main Street Historic Chestertown (MSC) is seeking an Executive Director to help guide the next chapter of our revitalization efforts. We are looking for a leader who understands the Main Street approach and values both vibrancy and belonging. We see MSC as a place of gathering, memory, commerce, and connection. This role is about stewardship, bringing vision, energy, and follow-through to a downtown that already has a big heart and is looking to build momentum.

About Main Street Historic Chestertown (MSC)

Main Street Historic Chestertown is a nonprofit organization committed to strengthening and preserving the best of our town. As both a Designated Main Street Maryland community and an Accredited Main Street America program, MSC operates within a nationally recognized framework for downtown revitalization. These designations reflect strong leadership and a commitment to long-term sustainability.

Our work blends historic preservation, small business support, placemaking, community events, and partnership-building. We collaborate closely with the Town of Chestertown, Washington College, local entrepreneurs, volunteers, and regional partners to ensure downtown remains healthy, welcoming, and economically resilient.

The Role

The Executive Director is responsible for the overall leadership and daily management of MSC, working closely with an engaged Board of Directors, downtown businesses, volunteers, local government, and community partners. The work aligns with the National Main Street Center’s Four-Point Approach: Organization, Design, Promotion, and Economic Vitality.

Core Responsibilities

• Provide nonprofit administration and financial management, including budgeting, reporting, and organizational compliance
• Partner closely with the Board of Directors to advance strategic priorities, support board development, and ensure strong governance practices
• Lead strategic planning efforts and guide implementation of board-approved goals
• Lead fundraising initiatives and oversee grant management and compliance
• Supervise staff, consultants, interns, and volunteers
• Engage and support downtown businesses and property owners
• Coordinate MSC committees and align volunteer efforts with organizational strategy
• Represent MSC at public meetings, community events, and partner gatherings
• Oversee marketing and communications, including website, social media, and press
• Collect, analyze, and report data to measure program effectiveness and maintain strong standing with Maryland Main Street

Desired Qualifications

• Experience with a Main Street program or downtown revitalization strongly preferred
• Background in nonprofit leadership, economic development, commercial district management, or related fields
• Ability to balance strategic vision with practical execution
• Strong written and verbal communication skills
• Comfort working across sectors and building collaborative partnerships
• Appreciation for historic preservation and small-town character

We are seeking an experienced leader who can see the big picture and move ideas forward—someone who understands that dynamic downtowns foster both economic opportunity and community belonging.

Salary Range

$75,000–$90,000, commensurate with experience

This is a full-time, exempt position. While evening and occasional weekend presence is required for events and community activities, MSC supports schedule flexibility and autonomy consistent with nonprofit leadership roles.

At this time, Main Street Historic Chestertown is not able to offer employer-sponsored health or retirement benefits. The organization recognizes the importance of benefits and is actively exploring options as MSC continues to grow.

Apply Today

To apply, please send a single PDF containing your cover letter, resume, and references to no later than March 27, 2026.

Main Street Historic Chestertown is an Equal Opportunity Employer.

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