Main Street Chestertown

Preserving History, Fostering Growth

Main Street Historic Chestertown is at the heart of the town’s revitalization efforts, focusing on preserving its rich history while fostering economic growth and community development. Through Main Street America’s Four-Point Approach, Chestertown has established a strong organizational foundation, with a dedicated team working to coordinate revitalization efforts and engage stakeholders.

Promotion is key to Main Street Chestertown, as it highlights the town’s unique assets and attractions to attract visitors and customers. The program also emphasizes the design of the downtown area, enhancing its physical appearance through historic preservation and beautification efforts.

Economic vitality is a central goal of Main Street Chestertown, which works to support existing businesses, attract new businesses, and create a diverse mix of commercial offerings. By strengthening the local economy and preserving its historic charm, Chestertown’s Main Street is helping to create a vibrant, sustainable community for residents and visitors alike.

Downtown Chestertown Street outside The Kitchen at the Imperial Restaurant with outdoor seating and orange umbrellas and an "Open" Flag Sign

Eastern Shore
Life at its Best

Main Street Historic Chestertown Inc. is a 501(c)3 non-profit organization which is dedicated to preserving, enhancing, and promoting historic downtown Chestertown, Maryland. Come experience Eastern Shore life at its best!


Main Street Chestertown will play a pivotal role in driving the expansion and diversification of thriving businesses within the downtown area.


Main Street Chestertown aims to actively promote the growth of the downtown community by fostering an uptick in the residential population.


To promote and support a diverse range of educational, cultural, entertainment and recreational activities that attract both residents and visitors to downtown.



Enrich the streetscapes and waterfront of the downtown area, cultivating a welcoming environment for both residents and professionals alike.


Facade Improvement Grants

Historical Landmarks

Downtown Businesses

Events Hosted Since 2018

Our Partners

Main Street Chestertown is proud to be a part of Main Street Maryland, the Main Street America, and the Department of Housing & Community Development. These partnerships help us implement our revitalization efforts and promote development in Chestertown.

Main Street Maryland: Learn more about Main Street Maryland and their role in supporting local Main Street programs across the state.

Main Street America: Discover the National Main Street Center and its commitment to revitalizing historic commercial districts across the country.

Maryland Department of Housing & Community Development: Find out more about the Maryland DHCD and their initiatives to strengthen communities and expand affordable housing options.


Coming Soon!

Meet The Board

Our board members are dedicated community leaders who are passionate about preserving and enhancing the historic charm of Chestertown. Get to know the individuals guiding our efforts! We are grateful for their commitment to our community and their efforts to make Chestertown a vibrant place to live, work, and visit.

Nina Fleegle, Executive Director of Main Street Chestertown

Nina Fleegle

Executive Director

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Kelly Reed

Assistant Director

Kristen Owen, President of Main Street Chestertown

Kristen Owen


Renee Bench, Vice President of Main Street Chestertown

Renee Bench

Vice President

Anne Forrest, Treasurer of Main Street Chestertown

Anne Forrest


Rebecca Clark, Board Member of Main Street Chestertown

Rebecca Clark

Board Member

Paul Heckles, Board Member of Main Street Chestertown

Paul Heckles

Board Member

Anne Forrest, Treasurer of Main Street Chestertown

John Hutchison

Board Member

Meghan Livie, Board Member of Main Street Chestertown

Meghan Livie

Board Member

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Amy Meade

Board Member

Mike Smith, Board Member of Main Street Chestertown

Mike Smith

Board Member

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Amanda Williams

Board Member

Sarah Wright Board Member of Main Street Chestertown

Sarah Wright

Board Member

Liddy Campbell Vandemark, Board Member of Main Street Chestertown

Liddy Campbell Vandemark

Board Member

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