Welcome to Chestertown

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Where History Meets Modern Charm

Founded in 1706 as a bustling port town on the scenic Chester River, Chestertown quickly became a hub of commerce, exporting tobacco, grain, and other goods that fueled the growing colonies.

Chestertown’s historical significance extends beyond trade. In 1774, it made history by hosting the Chestertown Tea Party, a bold act of protest against British taxation, echoing the spirit of the American Revolution.

The 19th century brought further prosperity and cultural development, marked by the founding of Washington College in 1782. Today, the town’s historic district showcases beautifully preserved 18th-century architecture, offering a glimpse into its colonial past.

Despite its rich history, Chestertown is more than a relic of the past. It is a vibrant community that continues to evolve while preserving its heritage. The town’s picturesque waterfront, thriving arts scene, and friendly atmosphere make it a delightful place to visit and call home.

Whether you’re strolling along the brick sidewalks of our historic district, exploring our art galleries and boutiques, or enjoying the natural beauty of the Chester River, Chestertown offers a warm welcome and a glimpse into a bygone era. Come and discover the charm of Chestertown, where history comes alive.

Historic Map of Chestertown
Historic Map of Chestertown
Historic Chestertown Building
Historic Postcard Paving Chestertown
Historic Image of Downtown Chestertown

How to Get Here

From the North

To reach Chestertown, Maryland, from points north such as Philadelphia or New York, take I-95 South to the Middletown/Route 896 exit (1A). Merge onto Route 896, which merges with Route 301 South. Take the Galena exit (Route 290 South) and turn right. At the stoplight, continue straight onto Route 213 South into Chestertown.

From the West

For travelers coming from points west like Washington D.C. or Baltimore, take your preferred route to Routes 50/301 East and follow signs for the Bay Bridge/Annapolis. Stay on Routes 50/301 as you cross the Bay Bridge and continue on the Eastern Shore. Pass through Queenstown and proceed north on Route 301. Exit Route 301 at Route 213 and continue north.

From the South

If you’re traveling from points south such as Northern Virginia, take either the Washington Beltway (I-495), I-95, or Route 301 to Routes 50/301 East. Follow Routes 50/301 across the Bay Bridge to the Eastern Shore. Continue on Routes 50/301 and head north on Route 301 after passing through Queenstown. Exit Route 301 at Route 213 and head north. In Chestertown, Route 213 becomes Washington Avenue. By turning left on Cross Street, you’ll be right downtown!

Happy Anniversary, Goddess Hebe!

Fountain Park, in the center of Chestertown, is located at the corner of High and Cross Streets. The centerpiece fountain, “Lady in the Park”, topped with the Greek goddess of youth Hebe, was cast in the late-1800’s in Philadelphia by Robert Wood and Company  sometime between 1866 and 1878. It has been a Chestertown landmark since 1899, when the Ladies Improvement Society, later to become the Chestertown Garden Club, purchased it from a park in Wilmington. This year, the Fountain will celebrate its 125th Anniversary in early August with an event in the Park. 

Founded in 1706

Chestertown was founded in 1706, officially established by colonial charter as part of Queen Anne’s County, Maryland. It was originally known as “New Town” or “Newtown” and was intended to serve as a port and trading center along the Chester River, which flows into the Chesapeake Bay. The town’s location made it an ideal hub for trade and commerce in the region.

By the mid-18th century, Chestertown had become a bustling port town, exporting tobacco, grain, and other goods to Europe and the Caribbean. It also became a center for shipbuilding, with many vessels constructed along its waterfront.

During the American Revolution, Chestertown was a hotbed of revolutionary activity. In 1774, the residents of Chestertown staged the Chestertown Tea Party, in which they protested British taxation by throwing tea into the Chester River, in imitation of the Boston Tea Party.

Chestertown is home to Washington College, which was founded in 1782 and is the 10th oldest college in the United States and the oldest college in Maryland. It was founded under the patronage of George Washington, who donated 50 guineas to the college and served on its Board of Visitors and Governors.

After the Revolution, Chestertown continued to thrive as a center of trade and commerce. In the 19th century, it became known for its manufacturing industries, including textiles, shoes, and canned goods. The town’s economy also benefited from its location on the Eastern Shore of Maryland, which made it a transportation hub for goods moving between Baltimore, Philadelphia, and other cities.

Today, Chestertown is known for its historic architecture, charming streets, and vibrant arts scene. It remains an important cultural and economic center on Maryland’s Eastern Shore.


Chestertown Tea Party


The Chestertown Electric Company is founded, bringing electricity to the town.


The Chestertown Historic District is established


The RiverArts organization is founded


First annual Legacy Day celebration


The Chestertown Spy launches

Officially established by colonial charter


Washington College founded under the patronage of George Washington


The Hebe Fountain is installed in Fountain Park


The Schooner Sultana is launched


Chestertown hosts the first annual Downrigging Weekend!


Chestertown opens a town marina & the Cerino Center


Come Visit Us!

Discover the insider knowledge on where to find the best cream of crab soup in town, indulge in the tastiest ice cream, and plan your visit to the art galleries. Let us guide you to create a spectacular experience in Chestertown that combines culinary delights, sweet treats, and a journey through the town’s vibrant art scene.

Immerse yourself in the local flavors with a bowl of the town’s renowned cream of crab soup, savor the sweetness of handcrafted ice cream, and explore the rich culture of Chestertown through its diverse art galleries. Let us be your tour guide!

The Chestertown Chat

Experience Chestertown’s colonial charm through our dedicated blog. Join us as we bring you firsthand accounts from enthusiastic visitors and passionate residents who have fallen in love with our historic town. Discover the hidden gems, explore the rich heritage, and immerse yourself in the stories that make Chestertown truly special. Stay connected and be inspired by the captivating narratives that unfold on our Chestertown Chat!