Downtown master plan

downtown chestertown master plan

Main Street is embarking on a Downtown Master Plan with our local partners and a consulting firm to plan 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, utilities, tourism, and more. Master planning recognizes the importance of forethought and community engagement and the effect pre-planning has on greater future outcomes. The Town of Chestertown is working off of a 2015 Comprehensive Plan, which states a “General Commercial Goal” of “maintain the vitality of the central business area as a prosperous commercial center.” However, the Comprehensive Plan does not illustrate any responsibilities, strategies, or implementation plans related to this goal and the last Downtown Master Plan was published over 50 years ago, and there has been no documented master planning since.The purpose of the Downtown Master Plan will be to develop a vision, strategy, list of projects, and implementation plans to bring this goal to fruition. As Chestertown prepares for its future, the Master Plan will be the guiding document for all major downtown decisions, as well as a beacon for private owners and investors to utilize as they prepare to market their properties or plan improvements.

Downtown projects occurred in recent years in spite of the lack of a Master Plan and have not had the benefit of an overarching vision and plan to ensure ongoing development is holistic, sustainable, robust, and cohesive. Recent projects may be seen as “one-offs” rather than progress towards a greater future vision, while high level needs such as resilient infrastructure and state-of-the-art streetscape designs go under-financed. Signs of planning and targeted investment deficiencies include a 5% decline in Chestertown population 2010-2020, continuing concerns with the quality of Kent County public schools, and long term commercial vacancies just outside the downtown district.

Examples of community investment needs include:

  • stormwater management,
  • mitigation of overhead electric/phone/internet wires,
  • sea level rise resiliency,
  • bike and pedestrian pathway planning,
  • infill property development prioritization,
  • public space planning and the balance between parking and pedestrian uses,
  • residential (especially workforce housing) planning,
  • preservation of Colonial and Victorian properties and landmarks,
  • street and curb design for traffic calming and  vehicular/pedestrian circulation,
  • pedestrian and vehicular wayfinding,
  • storefront, sidewalk, and street lighting,
  • streetscape improvements (e.g., sidewalk, outdoor seating, planting/tree canopy)

The single overarching long term community investment need is a plan for the revitalization of downtown Chestertown to ensure its prosperity and vitality for the next twenty to forty years.

Request for Qualifications

Main Street Chestertown is seeking qualification statements in the form of a Request for Qualifications from interested consultants to provide professional planning and related design services to prepare a Master Plan for Downtown Chestertown, MD.

Proposals with all requested supplementary information must be received by 4:00 p.m. EST, November 30, 2023 in digital format only. Information about how to submit is included in the RFQ packet.

All questions must be received via email ( by November 15, 2023. It is the intent of MSC to contact all prospective consultants on or by December 30, 2023. For shortlisted firms, additional information and direction will then be provided.

MSC reserves the right to reject any or all proposals, or accept any proposal determined to be in the best interest of MSC to fulfill its goal in creating the desired master plan.

Request for Qualifications packets and Supporting Documents may be obtained below. Included in the Supporting Documents is a timeline, maps, reports, correspondence, photographs and related information to familiarize prospective consultants with the scope and context of the Project. A site visit to Chestertown is highly recommended and tours will be scheduled on an individual basis. All interested parties are encouraged to visit. For more information/questions, please contact



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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


Chestertown Town Hall
118 N. Cross Street
Chestertown MD 21620


PO Box 427
Chestertown MD 21620

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