Main Street Chestertown

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.

Our Goals

Goal #1

Main Street Chestertown will facilitate an increase in the number and variety of successful downtown businesses

Goal #2

Main Street Chestertown will encourage an increase in the number of residents in the downtown area.

Goal #3

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

Goal #4

Main Street Chestertown will enhance downtown’s streetscapes and waterfront to create an inviting living and working environment.


Nina Fleegle, Executive Director
Kelly Reed, Assistant Director

Board of Directors

Kristen Owen, President
Renee Bench, Vice President
Anne Forrest, Treasurer
Amy Meade, Secretary
Mike Smith, Board Member
Liddy Campbell, Board Member
Meghan Livie, Board Member
John Hutchison, Board Member
Rebecca Clark, Board Member
Sarah Wright, Board Member
Paul Heckles, Past President

Get In touch


P.O. Box 427
Chestertown, MD 21620