Main Street Historic Chestertown is Hiring: Executive Director

Job Description

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. The MSC Board of Directors is seeking a highly organized, detail-oriented, self-starting individual for its full-time Executive Director position.

The Executive Director (ED) of MSC is responsible for the management, coordination, administration, documentation, and implementation of MSC's revitalization program, following the National Main Street Center's Four-Point approach:

  • Organization - Managing the operational aspects of a non-profit organization, extensive fundraising efforts, and building consensus and cooperation among the volunteers, businesses, residents and organizations that all play roles in the MSC District

  • Design - Enhancing and improving the appearance of the MSC District in accordance with the Master Plan, utilizing urban design and historic preservation initiatives

  • Promotion - Marketing the MSC District to investors, new businesses, residents, local employees, shoppers and visitors

  • Economic Vitality - Strengthening, building and diversifying the economic base of the MSC District

Application Instructions

To apply, please send a single PDF containing your cover letter, resume and references to employment@mainstreetchestertown.org no later than April 15, 2021.

About Main Street Historic Chestertown

In downtown Chestertown, it’s all around. We may not have a street labeled “Main,” but we do have a nationally recognized Main Street program whose volunteers work with other local organizations to keep our historic downtown district attractive and vibrant.

As a Main Street community, we’re part of a national network of historic downtowns created by the National Trust for Historic Preservation. Our 501(c)(3) nonprofit is guided by the Trust’s tested model for revitalization as we work to improve streetscapes, support our unique shops and restaurants, attract new ones, and create fun events that draw people downtown. The State of Maryland’s Main Street office provides guidance, staff training and resources. Read about the national Main Street program here.  And check out Maryland’s Main Street communities here.

Learn more about Main Street Historic Chestertown.


As a benefit to our members, the Kent County Chamber of Commerce is pleased to offer special job postings for businesses that are seeking employees.

If you are a member of the Kent County Chamber and would like to take advantage of this opportunity, contact executive director Sam Shoge at sshoge@kentchamber.org.


About the Kent County Chamber of Commerce

With more than 300 member businesses, nonprofits, and individuals, the Chamber is Kent County’s premier business-to-business facilitator. Through our many unique programs, events, and advocacy, we provide a platform for leaders from the private, public, and non-profit sectors to engage with each other to grow their respective organizations for the ultimate benefit of Kent County and its residents. 

Interested in joining? Learn about the benefits of becoming a member today.