African American Heritage Walk and self-guided tour - download: Book Brochure

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Chestertown, Maryland: An American Hometown for More than 350 Years

July 28, 2024 2pm - 4pm

There's nothing like going to the movies on a hot summer day. Join us to watch a 1995 film documenting life in Chestertown at two moments in our history.

Our new site is still under construction. Stay tuned!

Home Events Exhibits History Research About Us Contact



Chestertown, Maryland: An American Hometown for More than 350 Years

July 28, 2024 2pm - 4pm

There's nothing like going to the movies on a hot summer day. Join us to watch a 1995 film documenting life in Chestertown at two moments in our history.

Home Events Exhibits History Research About Us Contact


Chestertown, Maryland: An American Hometown for More than 350 Years

July 28, 2024 2pm - 4pm

There's nothing like going to the movies on a hot summer day. Join us to watch a 1995 film documenting life in Chestertown at two moments in our history.

The Historical Societyof Kent County

Kent County History at a Glance

Kent County’s documentary history starts in 1608, when the first Chesapeake Bay mapping expedition, led by Captain John Smith, mapped the Sassafras River, the county’s northern border today. In 1642, Maryland’s governor and council formally established Kent County at Kent Island and encompassing nearly the whole Eastern Shore. As settlements increased, smaller counties formed within the region, and, in 1675, the Kent County seat was moved to near Chestertown.

In 1706, Chestertown was named a Royal Port of Entry, making it the primary port for the upper Eastern Shore and leading the county to flourish in trade, culture, shipbuilding and agriculture. A significant part of Kent County’s prosperity in the 18th and 19th centuries was the work of enslaved people, but also that of free black entrepreneurs, laborers and artisans who, by 1850, were more than a quarter of the county population.

Kent County also lay along the shortest route from Virginia to Philadelphia, making it a stopover site for several founding fathers, including George Washington. In the mid- to late 18th century, many substantial homes and businesses were built, and today Chestertown has the largest number of 18th century buildings in Maryland, except for Annapolis. 

Visit Us

Our home is in the heart of Chestertown’s National Historic District at the Bordley History Center, at the corner of High and Cross Streets (301 High St), itself a historic building rebuilt in 1910 after a devastating fire swept through our commercial downtown.

Regular hours:

Thursdays: 11 am – 2 pm

Fridays: 11 am – 2 pm

Saturdays: 10 am – 1 pm 

First Fridays 5 pm – 7 pm

Our Mission

The Historical Society of Kent County, Maryland, is a non-profit organization dedicated to the collection and preservation of artifacts, documents, and information that aid in the interpretation of all aspects of Kent County’s history. The Society shares this information through its research library, museum space, programs, publications, and website in order to foster a knowledge and understanding of the shared heritage of our community. The Society supports and encourages the preservation of historic buildings and sites throughout Kent County.  

Learn more about The Historical Society.

Walking Tours


Chestertown’s walking tour of its iconic historic homes now has a paperless alternative.

The original Architectural Tour was commissioned by the Town of Chestertown and was written by local historian Robert J.H. Janson-LaPalme.  The Tour has been a staple for Historic Downtown Chestertown visitors since it first appeared in 1985. The Society’s online version is produced with permission of the Town.

The paper version of the Tour will continue to be available through the Kent County Office of Tourism, the Visitors Center on Cross Street, and the Bordley History Center at 301 High Street.

Please click here to enjoy the Walking Tour!


The Historical Society also offers guided walking tours! For more information, please contact us.


Open now: Galena, Gem of North Kent County

Produced in partnership with the town of Galena, and made possible by funding from Stories of the Chesapeake and the Maryland Heritage Areas Authority. 

Beginning with its founding in the mid-18th century, this exhibit traces the history of the town that has been called “the gem of North Kent County.” Visitors will learn about Galena from the colonial era to the 21st century, including the famous ride of Tench Tilghman, aide-de-camp to General George Washington, who carried the news of the end of the Revolutionary War to the Continental Congress in Philadelphia. Artifacts and photographs from Galena’s past are also included. 

Research and writing by Barbara Jorgenson and Amber Englebach, design by Amber Englebach. 

Additional exhibits produced by the Historical Society are on display throughout the county: at Chestertown Marina’s Cerino Center, the  Kent County office building, and at the Galena branch of the Kent County Public Library. 

For past exhibit brochures, click here.

Upcoming Programs & Events

Film Screening: Chestertown and Kent County, 1940 – 1995

Chestertown, Maryland: An American Home Town for more than 350 years 

featuring excerpts from the 1940 film”Chestertown, Maryland: A Classic American Town on the Chester River”

July 28, 2024, 2 pm – 4 pm at Emmanuel Episcopal Church Parish Hall, 101 North Cross Street, Chestertown 

Click here to reserve your seat

There’s nothing like going to the movies on a hot summer day! Join the Historical Society for a look back at life in Chestertown in very different parts in the 20th century. 

With commentary from local residents and luminaries of the day, the video shows slices of life in Chestertown and Kent County in 1995 as well as substantial footage from a “prequel” produced in 1940. The result is an immersive dual time capsule from two moments in time over half a century apart. 

The 1940 film is a treasure trove of scenes from life in Kent County before World War II, from streetscapes to fashion, people, businesses, celebrations, and pastimes. A highlight is the children’s pet parade, complete with dogs in bonnets, kittens, goats, a duck, at least one raccoon, and much more.

By 1995, Kent County’s economy was thriving and beginning to focus on heritage tourism. The film includes appearances by pillars of the Kent County community of the day, whose ideas and actions still influence life here today, including longtime mayors Elmer Horsey and Margo Bailey. Locals share memories sparked by scenes from 1940 and offer their perspectives on Chestertown’s history as well as thoughts about where we’ve been, and where, in 1995, they see the community going. 

The screening will be followed by a brief discussion about life in Kent County in earlier eras. Bring your memories and stories to share! People who appeared in the film and their relatives are especially invited to attend and participate. 

Admission is free, but your donations help us continue to present programs and events sharing, celebrating, and reflecting on Kent County history. Please consider making a contribution today.  

Click here to reserve your seat


Celebrate Legacy Day at the Historical Society 

We are proud to host this year’s Legacy Day exhibit, produced in collaboration with Sumner Hall:

African American Fraternal and Service Organizations of Kent County 

On display for the month of August

Opening reception: First Friday, August 2, 5 – 7 pm


The Historical Society of Kent County Library collection includes thousands of items pertinent to regional history including reference works, manuscript collections, documents, ledgers, maps, genealogies, cemetery records, photographs, and oral histories.

Learn More


The Historical Society of Kent County always welcomes new members. You do not have to live locally to join; a number of our members support our efforts from afar. If you are a resident, however, we hope you will not only become a member, but join us at our events and activities, or consider volunteering. We offer a welcoming venue for community involvement for all ages. A donation of $25 is required for an individual membership, and a donation of $40 is required for a family membership. Student memberships are free.

Register online securely now with Square or send your check to our office at P.O. Box 665, Chestertown, MD 21620.  Please include your email address as we communicate with our members primarily by email.

Learn More


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