Downtown Master Plan Release

Press Release

March 25, 2024

Main Street Chestertown and local partners are embarking on a Downtown Master Plan with Design Collective, Inc., a Baltimore-based consulting firm, to envision the future of Chestertown’s Historic District. Working in concert with the Town’s Comprehensive Plan and the Town’s Strategic Agenda, the Downtown Master Plan will focus on multiple aspects, including infrastructure, streetscape, land use planning, tourism, and more. 

The Downtown Master Plan will develop a holistic, sustainable, and cohesive vision for Chestertown’s future and identify key projects necessary to accomplish the vision. It will promote the economic growth necessary for Chestertown to thrive for decades to come while preserving Chestertown’s uniqueness and charm. The Downtown Master Plan will be the guiding document for all major downtown decisions and a beacon for private owners and investors to utilize as they prepare to market their properties or plan improvements.

Starting this month, Main Street Chestertown has partnered with Design Collective on a six-month “Phase 1” planning effort that will include data collection, community input, and visioning. Stakeholders from every part of the community will be included in the process, including the public at large. Phase 1 will inform Phases 2 and 3, which will include project development, funding, and implementation. 

Nina Fleegle, Executive Director of Main Street Chestertown, states, “The Downtown Master Plan is imperative for giving not only Main Street Chestertown, but all parties working toward a healthy, historic downtown, a roadmap for the near future. The plan will ensure that the “feel” and uniqueness of Chestertown is preserved for many years to come.”

“Design Collective, along with our civil engineering team member George, Miles & Buhr, LLC (GMB), love working with small towns where there is an appreciation of history, culture, arts, and the natural environment to build upon. We look forward to working with Chestertown stakeholders in a collaborative, engaging process that sets in place a visionary, yet implementable master plan,” says Cecily Bedwell of Design Collective.

For more information about the Downtown Master Plan, visit Main Street Historic Chestertown Inc. is a 501(c)3 non-profit organization dedicated to preserving, enhancing, and promoting historic downtown Chestertown, Maryland. Design Collective is an award-winning multi-disciplinary design firm with a diverse portfolio of successful projects throughout the United States and abroad. The firm offers expertise and national leadership in the disciplines of architecture, planning, urban design, landscape architecture, interior design, sustainability, and ensuring comprehensive design solutions.

You may also like…


Submit a Comment

Your email address will not be published. Required fields are marked *

Placeholder Image

Chestertown, Maryland was founded in 1706. It was established as a port town and played a significant role in the colonial era, serving as a bustling trade hub along the Chester River. Today, Chestertown retains much of its historic charm and is known for its well-preserved 18th-century architecture and vibrant cultural scene. Thanks for checking us out!



(410) 778-2991


Kent County Visitors Center
2nd Floor
122 N. Cross Street
Chestertown MD 21620


PO Box 427
Chestertown MD 21620

Main Street Chestertown would not be possible without the support of our partners:

Site Credit | Copyright © 2023 - 2024 Main Street Chestertown. All Rights Reserved.