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Chestertown, Maryland
A Historic River Town Worth Exploring
Set along the Chester River, Chestertown is one of the Eastern Shore’s most distinctive destinations—where colonial streets, waterfront views, and a lively arts scene come together in a way that feels both timeless and vibrant.
Founded in the early 1700s as a port and county seat, Chestertown quickly became one of Maryland’s most important colonial towns. Its location on the Chester River made it a hub for tobacco and grain exports, and many of the elegant brick homes and buildings from that era still stand today.
The town also holds a unique place in Revolutionary history. In 1774, local residents organized protests against British taxation—events now commemorated each year during the Chestertown Tea Party Festival. While parts of the famous “tea tossing” story are debated by historians, the spirit of resistance and independence remains central to the town’s identity.
As you walk through downtown, you’re moving through one of the best-preserved historic districts in Maryland, where Georgian and Federal-style architecture creates a setting that feels unchanged for centuries.
Just a short drive from Still Pond Inn, it’s the kind of place where you can spend a full day wandering—moving from historic landmarks to local shops, from waterfront sunsets to seasonal festivals.
Upcoming Events in Chestertown, Maryland
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What to Do in Chestertown
Stroll the Historic Downtown
Chestertown’s downtown is compact, walkable, and full of character. Brick sidewalks lead past boutiques, galleries, bookstores, and cafés, all set inside beautifully preserved buildings.
Explore the Waterfront
The Chester River is central to the town’s charm. You can:
- Walk along the marina and waterfront paths
- Watch sailboats drift by
- Catch sunset views over the water
- Attend seasonal events right on the river
Discover Local History
For those interested in deeper stories, Chestertown offers a layered past:
- Colonial trade and maritime life
- African American history and heritage sites
- Museums like Sumner Hall and the Kent County Historical Society
Visit Washington College
Founded in 1782 with support from George Washington, Washington College is one of the town’s defining landmarks. Its campus blends historic architecture with open green space and often hosts lectures, performances, and cultural events.
Fun Fact: Washington College is the only college that can say it got George Washington’s personal approval to use his name. He didn’t just agree to it—he donated money to the school and even served on its governing board, making it the only college he was directly involved with during his lifetime.
Festivals and Events
Plan your trip around Chestertown’s most memorable moments
Chestertown’s calendar is packed with celebrations that bring the town to life throughout the year. If you’re planning a visit, these are worth timing your stay around.
National Music Festival
A two-week classical music celebration featuring performances from world-class musicians and rising artists.
Chestertown Tea Party Festival
The town’s signature event celebrates its Revolutionary roots with parades, reenactments, live music, and waterfront festivities.
Downrigging Weekend
One of the largest tall ship gatherings in North America. Historic ships line the river, accompanied by music, food, and maritime culture.
First Friday
Art walks with extended shop hours and live entertainment
Dickens of a Christmas
A festive transformation of downtown into a Victorian holiday scene, complete with costumes, carolers, and seasonal markets.
A Living, Modern Town
While deeply historic, Chestertown is far from a museum piece. Today, it’s a lively small town with:
- A strong arts and culture scene
- Local restaurants and cafés
- A growing mix of shops and galleries
- Community events year-round
Its connection to Washington College and its active downtown give it an energy that’s rare for a town of its size.
Why Visit from Still Pond Inn
Chestertown offers the perfect complement to a stay at Still Pond Inn:
- Close enough for an easy day trip
- Rich in history without feeling crowded
- Scenic, relaxed, and authentically local
- Ideal for dining, shopping, and exploring
Whether you’re interested in history, waterfront views, or simply wandering somewhere beautiful, Chestertown is one of the Eastern Shore’s most rewarding places to explore.
Plan Your Visit
From quiet morning walks to lively festival weekends, Chestertown changes with the seasons—but always keeps its sense of place.
Spend a few hours, or make a day of it. Either way, it’s a stop that tends to linger long after you leave.
