Chestertown Main Street releases visionary Phase One Master Plan

After more than a year of community engagement, design work, and collaboration with the town of Chestertown, Main Street Chestertown has officially released its Downtown Master Plan: Phase One Report. The comprehensive 179-page document outlines a long-term vision for revitalizing and improving the town’s historic downtown district through a set of 40 proposed infrastructure and placemaking projects.

Paul Heckles, who has helped lead the initiative, explained that the process began nearly three years ago when Main Street Chestertown first began conceptualizing a master plan. “That led to a couple of years of planning,” Heckels said. “Eventually, we posted a request for proposals from consulting firms, and we hired Design Collective out of Baltimore.”

The project formally launched in February 2024, following a competitive RFQ process that drew interest from 12 firms. Design Collective was selected for its expertise in urban design and community-focused planning. What followed was a year-long effort that included workshops, creative brainstorming sessions, focus groups, and feedback loops with residents and stakeholders.

The result, now available here as a digital flipbook and downloadable PDF, outlines 40 conceptual projects that aim to reshape the downtown experience—ranging from burying utility wires and improving the tree canopy to reimagining sidewalks and restructuring the parking system for greater efficiency and accessibility.

“These 40 projects are pretty significant infrastructure projects,” said Sonni Huntzinger, Executive Duerctor of Main Street Chestertown. “Each one will require its own engineering and design throughout the course of what we’re calling Phase Two.”

The plan is structured into three phases. Phase One, now complete, centers on visioning and conceptual project recommendations. Phase Two will focus on prioritizing and sequencing those concepts, moving selected projects into detailed schematic design and engineering, ready to be bid out for construction. Phase Three will be the implementation phase—moving projects from paper to pavement, complete with groundbreaking and ribbon-cutting ceremonies.

Throughout the planning process, Main Street Chestertown worked closely with the town’s leadership and an advisory board. The town contributed funding and input, and community engagement remained central. “The community really put a lot of effort into this,” Huntzinger noted, pointing to the various charrettes and workshops that shaped the final report. “It’s the community we want to say thank you to for this product.”

Heckles emphasized that the geographic scope of the report is centered on the historic district, but the ambitions of the plan go beyond physical improvements. “We hope it elevates the health and well-being of residents and visitors—anyone who spends time in downtown Chestertown,” he said. “We hope it addresses the need for a more diverse environment downtown, one where people of all walks of life are going to feel welcome and invited to participate.”

In addition to infrastructure, the plan also considers programming and communication strategies that will enhance the cultural and economic vitality of the area. As Huntzinger explained, “There’s a whole other layer that Main Street brings to it… It’s the impact these projects will have on quality of life and the downtown experience for visitors, residents, and businesses.”

The Phase One report is now publicly accessible, offering a transparent and detailed look into Chestertown’s aspirations for the next 5, 10, or even 15 years. As the town moves into Phase Two, the focus will shift to making those aspirations actionable.