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Eastern Shore Land Conservancy is committed to preserving and sustaining the vibrant communities of the Eastern Shore and the lands and waters that connect them.

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ESLC Walk of the Week: Bailey Park

In Chestertown’s 4th Wardshort walk from the Kent County Middle School, is an 18-acre park named after my mother (Margo Bailey). She was mayor of Chestertown for twenty years, beginning when I was in 4th grade until I was 30 years-old. It’s a modest park that is home to the Stetson Dog Park, a looping trail, small playground, and wide-open field full of potential.  

When I was growing up in Chestertown my favorite parks were Wilmer Park by the Chester River and the amazing community playground at H. H. Garnet Elementary School; the construction of which my mother helped organize before she became mayor. We lived right down the street and I joked with my friends that my mom built the playground for me in our town’s backyard. Today, that playground is gone, and so is my ability to run the wooden steps, jump across the bridges and, crawl through the tunnels. InsteadI enjoy walks with my wife, our daughter, and our small dog at Bailey Park, which is within walking distance of where we live.

Bailey Park is one of the largest parks in Chestertown and it serves a great need for the residents in the 1st and 4th wardit is the only park within walking distance, unless you count the track and workout stations at the Middle School. Bailey Park is a great place to take quiet walks with kids as the track is perfect for strollers. There is a small playground and though my daughter is too small for it now I know one day she’ll ask us to stop so she can play and of course we will say, ‘go have fun.’

Most of what Bailey Park has to offer is wide open space and all the possibilities that come with it. I like to think of Chestertown, and every town, as a constant work in progress. Like a garden, the town will continue to grow as people come and go. Each generation leaves behind part of their passion and influence in the community which sets the foundation for the next generation to build upon. I compare it to the young trees I’ve planted in my yard, the pleasant summer shade of which I may never get to experience, but a future generation will.  

That is what Bailey Park means to me — a gift from the previous generation that brings value and wealth to the community. It is up to us, and future generations, to continuously enhance these public spaces so they can continue to be enjoyed for generations to come.

All photos captured by Owen Bailey, Towns Project Manager.


About the Eastern Shore Land Conservancy

Eastern Shore Land Conservancy (ESLC) is a private, nonprofit land conservation organization committed to preserving and sustaining the vibrant communities of the Eastern Shore and the lands and waters that connect them.  For more information please visit www.eslc.org.

ESLC’s Center for Towns creates and promotes safe and equitable access to parks, trails, and other public spaces throughout the region. By highlighting these community assets, within and between Eastern Shore towns, we seek to increase public usage and support of public open spaces to ensure that all citizens have a deeper connection to land and place.

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