Eastern Shore Life at its Best

Main Street Historic Chestertown Inc. is a 501(c)3 non-profit organization which is dedicated to preserving, enhancing, and promoting historic downtown Chestertown, Maryland. Chestertown is located on Maryland’s Eastern Shore on the banks of the Chester River. Established in 1706, this small colonial town encompasses the arts, the environment, and history. Come experience Eastern Shore life at its best!




Fall 2022 Projects

Main Street is continually working hard to improve Chestertown. This Fall, look for: wayfinding signage for visitors, increased security monitoring, a large installation of historically appropriate lighting, commercial building facade renovations, small business mentoring for local businesses, streetscape clean up, and more. We encourage you to learn more about our current projects and help us to make Chestertown an amazing place to live, work, and play!

Stay up to date on all things Main Street Chestertown by signing up for our quarterly newsletter!


* indicates required

Featured Business

Bespoke Chocolates

Welcome to one of our newest businesses!

Bespoke Chocolate is your destination in Chestertown for chocolate and other sweet treats! Plus: Special events, custom chocolate designs, and more.

The Chestertown Chat

Follow our Chestertown blog to hear from visitors and residents who love our colonial town.

Explore Downtown Chestertown

Plan your trip to downtown Chestertown and see all that you can do within walking distance.

  • There are no listings matching your search. Reset Filters
  • Main Street Chestertown would not be possible without the support of our partners: