Main Street Chestertown

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!

Announcements

Friday, July 1 5-8pm

Join Main Street during July’s First Friday for a carnival! Attractions will include a trackless train, face painting and balloon animals, games & prizes, a magician and more! For more details, click on the image to the left. See you on the midway!

Shopping

Dining

Experiences

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.

Upcoming Events

Farmers' & Artisans' Market

300 High Street
June 25, 2022 8:00 am - 12:00 pm

Carnival on High

200 High Street
July 1, 2022 5:00 pm - 8:00 pm

Chestertown Car Show

200 High Street
October 1, 2022 12:00 pm - 4:00 pm

Explore Downtown Chestertown

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

Download Walking Map

Trip-Planning Resources:

Kent County Visitors Center

Bordley History Center

Washington College

The Sultana Education Center

Sumner Hall

Main Street Rock Hall

Kent County Parks & Recreation