About Us


Where is “Main Street”?

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.


Our Mission

Main Street Chestertown will foster an inviting, diverse and prosperous downtown.

Our Vision

Historic Downtown Chestertown is a welcoming and vibrant waterfront community where people of all ages are drawn to live, work, shop, and enjoy recreational and cultural activities in a beautiful setting.

Our Goals

1. Main Street Chestertown will facilitate an increase in the number and variety of successful downtown businesses.

2. Main Street Chestertown will promote and support a diverse range of educational, cultural, entertainment and recreational activities that attract both residents and visitors to downtown.

3. Main Street Chestertown will enhance downtown’s streetscapes and waterfront to create an inviting living and working environment.

4. Main Street Chestertown will encourage an increase in the number of downtown residents.


The Four-Point Approach

Main Street Chestertown follows the national model for community revitalization created by the National Trust for Historic Preservation. It calls for “Transformation Strategies” organized around four key areas, each supported by a working group: Organization, Economic Vitality, Design, and Promotion.

Organization involves creating a strong foundation for a sustainable revitalization effort. That means recruiting and supporting leaders for Main Street’s board and committees, cultivating partnerships, engaging the larger community, and providing resources – primarily funding and volunteers – for the work of the Main Street program.

Economic Vitality focuses on capital, incentives, and other economic and financial tools to assist businesses, catalyze property development, and create a supportive environment for entrepreneurs and innovators. Smart growth principles and reinvestment in existing properties are key to Chestertown’s success.

Design enhances the physical and visual assets that set the commercial district apart. In addition to celebrating and protecting downtown’s historic character, Main Street programs help create a lively and attractive streetscape that fosters walkability and makes everyone feel welcome.

Promotion initiatives communicate Chestertown’s strengths and charms through marketing, special events and storytelling. They support the shop-local-first experience and showcase why the community’s historical, educational, artistic, and environmental assets combine to offer Eastern Shore life at its best.

But wait, there’s more …. Clean, Safe & Green.  Since 2008, Main Street Maryland programs have also incorporated a Fifth Point: “Clean, Safe, and Green,” which focuses on “enhancing the perception of a neighborhood through the principles of Smart Growth and sustainability.” Main Street Historic Chestertown relies on — and where appropriate, partners with — the Town’s Environmental Committee for this aspect of downtown vitality. Learn more about the work of the Environmental Committee here.

Board of Directors

Executive Committee

Paul Heckles, President

Kristen Owen, Vice President

Anne Forrest, Treasurer

Renee Bench, Secretary



Megan Bramble

Carolyn Spencer Brown

Ellen Hurst

Barbara Jorgenson

Tom Kocubinski

Mike Smith