• Home
  • About
    • About Chestertown
    • Chestertown News
  • Visit
    • Plan Your Visit
    • Events
    • Chestertown Cash
    • Visitor’s Map
  • Businesses
  • Main Street
    • About Main Street Chestertown
    • Master Plan
    • Annual Report
    • Donate
  • Contact
Placeholder Image

Chestertown, Maryland was founded in 1706. It was established as a port town and played a significant role in the colonial era, serving as a bustling trade hub along the Chester River. Today, Chestertown retains much of its historic charm and is known for its well-preserved 18th-century architecture and vibrant cultural scene. Thanks for checking us out!

Stay in the know!

Join Main Street Chestertown's email list
for periodic updates and news about Chestertown.

Success!

Join the List

By clicking the subscribe button you agree to the Privacy Policy and Terms and Conditions.



Email

office@mainstreetchestertown.org



Phone

(410) 778-2991



Office

Kent County Visitors Center
2nd Floor
122 N. Cross Street
Chestertown, MD 21620



Mailing Address

PO Box 427
Chestertown, MD 21620

Main Street Chestertown would not be possible without the support of our partners:

Main Street America Logo in White
Maryland Department of Housing and Community Logo in White
National historic Trust
Historic Chestertown Logo in White
Main street Maryland logo in white
Site Credit | Copyright © 2023 - 2025 Main Street Chestertown. All Rights Reserved.
We use cookies to ensure that we give you the best experience on our website. If you continue to use this site we will assume that you are happy with it.Ok