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May 24, 2025

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Preserving the Heartbeat of Chestertown: A Chat with Nina Fleegle

November 13, 2023 by James Dissette

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As a holiday season busy with festive celebrations approaches, it’s a good time to remember that large town events require thoughtful planning and a concerted effort between multiple town and county organizations. Imagine coordinating parades, a Santa arrival, a Victorian makeover complete with horse-drawn carriages, and special downtown sales.

Key to this planning is Mainstreet Historic Chestertown, part of a network of coordinating communities formed by the National Trust for Historic Preservation in 1980 to revitalize historic downtowns across the US. The nonprofit had become a formidable national resource for helping historic communities thrive in its three decades of work.

The Chestertown Mainstreet organization was revitalized in 2015 as a nonprofit and administered for five years by Kay MacIntosh who set a high bar for presenting seasonal events.

Approaching her third year as Executive Director of Mainstreet Historic Chestertown, Nina Fleegle has furthered the commitment of the organization’s mission to preserve and promote Chestertown and “Create a place of shared prosperity, equal access to opportunity, and inclusive engagement.”

Fleegle sees traditional town events as vital but is looking beyond the immediate to help shape and employ a master plan.

“The plan, currently in its initial phase, involves hiring a consulting firm to gather community input, formulate a vision, and collect data. This initiative aligns with the recent town Council’s strategic agenda, emphasizing the need for a structured approach to long-term downtown vitality,” she says.

Subsequent phases of the master plan will delve into project details, prioritize initiatives, explore funding sources, and ultimately implement the plan. The town aims to unite stakeholders, including the public, nonprofits, and businesses, to ensure the sustained vibrancy of Chestertown’s downtown for the next 40 years.

The initiative has garnered community support, reflecting the shared commitment to making Chestertown a better place to live, work, and play. By strategically aligning efforts and resources, Main Street Chestertown aspires to secure a thriving downtown that stands as a testament to the town’s unique identity.

In the meantime, grab your top hat and brush up on your Dickens.

The Spy met with Nina last week to discuss current events and future planning.

This video is approximately seven minutes in length. For more about Mainstreet Historic Chestertown and to check their calendar, go here.

 

  

 

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

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Letters to Editor

  1. Nancy McGuire says

    November 13, 2023 at 4:44 PM

    I wish to point out that the National Trust Main Street program was initially created for towns that needed “revitalization”. It was felt that historic preservation could not occur unless town/businesses could afford to preserve their “main streets”. Chestertown never “needed” historic preservation revitalization, as you call it

    Chestertown (and Kent County) has been preserved over 300 years – generation after generation. We are fortunate to have inherited that generational dedication. The very value of our Town and County is based on that love and care over the years. As this value is recognized and embraced, I PRAY this new “Master Plan” by an outside “consulting firm” will not attempt to make us look like and function as every other Town. Uniform everything! That would be deadly. Chestertown is important because it is NOT like anywhere else. I am told over and over again that other Towns on Eastern Shore are now “packaged”, look alike and should be avoided except for an occasional visit. They find Chestertown totally refreshing. Why are we hiring an outside consultant? I have always been told that was Main Street’s job and expertise.

  2. Deirdre LaMotte says

    November 13, 2023 at 8:16 PM

    Nina is the perfect person for this job! She puts 100% of herself into
    all her endeavors and is a treasure for Chestertown. Well done.

  3. Paula Reeder says

    November 14, 2023 at 5:47 PM

    Together with Annapolis, Berlin, Middletown and Queen Anne’s Chestertown received it’s designation as a Main Street town from then Governor O’Malley and Secretary of Housing and Comminity Development Ray Skinner on June 29, 2008. In the interests of giving credit where credit is long overdue, this designation came largely as a result of Bill Ruckelshaus’ virtually singlehanded efforts to research, advocate and lead the designation application process in his capacity as the then president of the Downtown Chestertown Association. Bill believed strongly that Chestertown needed to take action to encourage heritage tourism and dedicated countless uncompensated hours to attending Main Street meetings and it’s 2008 Conference and coordinating with other Main Street applicants and local businesses to secure approval of Chestertown’s application plus $12,000 in start-up grant funding from the State. Subsequent to Chestertown’s designation as a Main Street town, Bill recruited Main Street Chestertown’s initial Director and Board of Directors and, subsequestly, stepped aside to let them get the program off the ground.

    Bill passed away in 2019. His efforts to establish what has, over the last 15 years, developed into a vibrant and lauded local Main Street Program have never been acknowledged by Main Street’s more recent administrators or Board. It’s about time he received the recognition he unquestionably deserves for being the true catalyst behind program implementation.

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