Main Street Manager
Main Street 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 is looking for a Main Street Manager to help support and shape one of Maryland’s most charming and beloved historic downtowns. Working closely with the Executive Director, Board of Directors, downtown businesses, and community partners, the Main Street Manager will help guide projects, support downtown initiatives, and contribute to the continued vibrancy of downtown Chestertown during an exciting period of growth and transition.
This role is ideal for a proactive professional who enjoys a balance of structured administrative tracking and active, public-facing community engagement, executing the vision of leadership to keep our historic downtown lovable and vibrant. One day might involve coordinating a grant reimbursement request, while the next could include helping with a ribbon cutting, supporting a beautification project, or brainstorming ways to make downtown feel even more vibrant and welcoming. It also means serving as one of our storytellers—whether you are snapping a photo for Instagram, drafting our community newsletter, or updating the website to keep everyone in the loop.
If you enjoy variety in your day, meaningful work, and being part of a close-knit community that cares deeply about its future, you might be our person.
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.
Core Responsibilities
Grant Coordination & Project Management
A significant portion of this role will involve grant coordination and project management, so we are looking for someone who enjoys organizing moving pieces and getting projects across the finish line. The Main Street Manager will help identify funding opportunities, assist with grant applications, manage reporting requirements, organize documentation, track deadlines, and support awarded projects from start to close-out. Experience with grants, nonprofit administration, or project coordination is strongly preferred.
The Main Street Manager will also support implementation of downtown initiatives including placemaking projects, beautification efforts, business support programs, and community activations. Some projects will be highly structured. Others may require creativity, adaptability, and figuring things out in real time—which is often part of the fun of Main Street work.
Business & Community Engagement
Downtowns are ultimately about people, and the best Main Street work happens when relationships are strong. The person in this position will regularly interact with business owners, entrepreneurs, volunteers, property owners, residents, nonprofit partners, and local leaders. We are looking for someone who is approachable, collaborative, responsive, and genuinely likes people. The Main Street Manager should feel comfortable building relationships, connecting stakeholders with resources, and helping create a welcoming environment for businesses and visitors alike.
A big part of keeping that environment vibrant is digital storytelling; you will manage a consistent content calendar that proudly features our small businesses, spotlights historic preservation initiatives, and highlighting local events, while promoting Main Street’s initiatives consistently.
Organizational Support
The Main Street Manager will work closely with the Executive Director and Board of Directors to help coordinate committees, support organizational priorities, and maintain momentum across a wide range of downtown initiatives. As a key voice for the organization, you will work hand-in-hand with the Executive Director to craft, amplify, and safeguard the distinct brand 'voice' of Historic Chestertown, ensuring all of our public messaging thoughtfully aligns with the strategic goals set by our Board. This may include assisting with meeting preparation, coordinating committee activities, maintaining project and grant records, tracking reinvestment statistics, and helping support volunteers and partnerships. The Manager role will also assist in maintaining the organization's central database(s), ensuring contact lists for businesses, stakeholders, and partners are consistently accurate.
Because Main Street organizations often juggle many overlapping initiatives at once, organization, adaptability, and a willingness to jump in where needed are all important qualities for success in this role.
Events
The Main Street Manager will help support initiatives that bring people downtown and strengthen community connections. This may include assisting with committee work, workshops, seasonal programming, downtown promotions, and community events. There will likely also be some event chaos - unpredictable weather, last-minute changes, or picking up things that somehow no one else remembered to pick up. Flexibility and a good attitude go a long way.
Some evening and weekend participation will occasionally be required, though the organization is committed to maintaining healthy work-life balance and a sustainable workload.
Qualifications
- Bachelor’s degree or equivalent experience in nonprofit management, community development, economic development, communications, marketing, public administration, or a related field
- 2–5 years of relevant professional experience preferred
- Experience with grant writing, grant administration, or project management strongly preferred
- Strong organizational skills and attention to detail
- Excellent written and verbal communication skills
- Ability to manage multiple priorities and work both independently and collaboratively
- Comfortable engaging with businesses, community stakeholders, volunteers, and partners
Proficiency with digital creation tools (e.g., Canva), email marketing software (e.g., Mailchimp), social media management suites, and standard office suites (Microsoft Office / Google Workspace) preferred, a willingness to learn required.
Position Details
- Schedule: 32 hours per week with flexible scheduling
- Salary: $50-60,000, annually based on experience
- Location: Chestertown (in-person presence is important for community engagement, with some flexibility available)
- Evenings/Weekends: Occasional, based on events and community activities
- Professional Development: Opportunities for training, conferences, and professional growth through Main Street and economic/community development networks
Main Street Historic Chestertown values sustainability in this role and is committed to maintaining a manageable workload within a 32-hour workweek structure.
Apply Today
To apply, please send a single PDF containing your cover letter, resume, and references to
employment@mainstreetchestertown.org
Main Street Historic Chestertown is an Equal Opportunity Employer.