Grab A Bite

Downtown Shopping

Dickens of a Christmas

Tea Party Festival – May 26-28, 2018


Where is “Main Street”?

In downtown Chestertown, it’s all around. We may not have a street labeled “Main,” but we do have a nationally recognized Main Street program whose volunteers work with other local organizations to keep our historic downtown district attractive and vibrant.

As a Main Street community, we’re part of a national network of historic downtowns created by the National Trust for Historic Preservation. Our 501(c)(3) nonprofit is guided by the Trust’s tested model for revitalization as we work to improve streetscapes, support our unique shops and restaurants, attract new ones, and create fun events that draw people downtown. The State of Maryland’s Main Street office provides guidance, staff training and resources. Read about the national Main Street program here.  And check out Maryland’s Main Street communities here.


Join the Main Street Team!

We are always looking for people who love Chestertown and are willing to lend their time and talent. If you are interested in volunteering, we’d love to hear from you! Email to manager@mainstreetchestertown.org. 


Chestertown: Eastern Shore Life at Its Best.