Where’s Main Street?    

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

What is Main Street Chestertown?

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. Our Volunteers contribute their time, talents, energy and resources to the operations, activities and events of Main Street Chestertown.

Our Vision

Downtown Chestertown is a vibrant place where locals love to live, work, and play, and where visitors choose to come time and again.

Our Mission

Main Street Chestertown will create a more engaging and prosperous downtown.

Our Goals...

• Main Street Chestertown will facilitate an increase in the number and variety of successful downtown businesses.
• Main Street Chestertown will market our waterfront assets and incorporate them into the life of downtown.
• Main Street Chestertown will promote and support cultural and recreational activities that attract both locals and visitors to downtown.
• Main Street Chestertown will enhance downtown's physical assets to create a more appealing living and working environment.

Dickens of a Christmas
Dec. 1-3, 2017

Find more event information at www.dickenschestertown.org

Click the event below to order tickets:
• Historic Holiday House Tour
• Whiskey Nightcap aboard the Packet

Click below for 5K Run/Dash registration:
• Run Like the Dickens
     ($5 discount coupons available at many                                Chestertown locations)


Contact Us:

Main Street Chestertown 
118 N. Cross Street  
Chestertown, MD 21620 

Program manager Kay MacIntosh, 410-778-2991.

The Town of Chestertown provides technical support and meeting space for the Main Street Chestertown program on the second floor of Town Hall. Learn More about this program and how you can help move Chestertown forward. Your contributions to Main Street Historic Chestertown are completely tax-deductible and totally appreciated (contact treasurer@mainstreetchestertown.org).