5 Reasons Why You Should Visit Chestertown, Maryland

5 Reasons Why You Should Visit Chestertown, Maryland

Recently, my day job took me to the small historic town of Chestertown, on Maryland’s Eastern Shore. The quiet beauty and historical elegance of the town impressed me so much that I thought I would share it with you via some photos.

Chestertown’s History

Chestertown, named for the Chester River, was founded in 1706. It enjoyed prominence as one of the Maryland colony’s six Royal Ports of Entry. By the middle of the eighteenth century, Chestertown was the second leading port in the colony. As such, it was a wealthy town, with a growing merchant class. Well off residents built brick mansions and townhouses along the riverfront.

Visit Chestertown Maryland: Elegant old townhouses line the streets near the riverfront.
Historic townhouses in Chestertown, Maryland (Source: By Acroterion – Own work, CC BY-SA 3.0)

Additionally, Chestertown is home to Washington College, the tenth oldest liberal arts college in the nation and the oldest college in Maryland.

The National Trust for Historic Preservation, the country’s largest private, nonprofit preservation organization, named Chestertown, Maryland, to its 2007 list of America’s Dozen Distinctive Destinations, an annual list of unique and lovingly preserved communities in the United States.

“Chestertown is a treasure hidden in plain sight,” said Richard Moe, president of the National Trust for Historic Preservation. “A small, historic and relatively unspoiled Eastern Shore town, Chestertown had the good sense to hang on to what makes it so special. The result is a vibrant community that offers travelers an ideal retreat.”

Need more convincing? Here are some of the reasons why you should visit Chestertown, Maryland:

1. Sultana

Visit Chestertown Maryland: The Schooner Sultana calls Chestertown home.
(Source: By Acroterion – Own work, CC BY-SA 3.0)

Chestertown serves as home port to a schooner named Sultana. Docked at the end of Cannon Street, Sultana was built largely by local volunteers. They used designs based directly on a 1768 Royal Navy survey of the original Boston-built merchant vessel, the smallest schooner ever in the British Royal Navy. Because the builders had access to the survey, it is one of the most accurate 18th century replicas in the world today. The ship offers educational tours for area schoolchildren, which are based on more than 2,000 pages of the original vessel’s log books, correspondence, and crew lists.

2. The White Swan Tavern

Visit Chestertown Maryland: The White Swan Tavern Bed & Breakfast

The White Swan tavern has been a fixture in Chestertown since before the Revolutionary War. It is conveniently located in the center of downtown, within walking distance of shops and restaurants, the Chester River waterfront, and the weekly Saturday farmer’s market.

In 1978, the property was impeccably restored to its 1793 appearance, with one room devoted to the display of many artifacts found in an archaeological dig on the site. During the entire process of restoration, the owners acquired pieces of furniture, both antique and reproduction, which they thought appropriate to the building. They furnished the remainder of the building with the ideals of simplicity and comfort in mind. Following painstaking analysis, the original paint color was reproduced for wall paneling and trim. A set of early chargers recovered from the tavern site became the models for the contemporary stoneware dishes.

Visit Chestertown Maryland: the White Swan Tavern is a colonial era bed & breakfast
Breakfast at the White Swan Tavern

The inn serves an afternoon tea and offers six deluxe rooms for rent. My personal favorite is the John Lovegrove Kitchen, which features a open beam ceiling and brick floor.

3. The Tea Party

One of my favorite festivals on the Delmarva Peninsula is the Chestertown Tea Party.

Delmarva Festivals: Celebrating the rebels of the American Revolution at the Chestertown Tea Party.
Image courtesy of Chestertown Tea Party Festival

In 1774, when the citizens of Chestertown learned that the British had closed the port of Boston in retaliation for Bostonians dumping tea into the harbor, they issued The Chestertown Resolves. The Resolves stated that it was illegal to import, sell or consume tea. Further, the citizens of Chestertown gathered at the town center, marched down High Street to the brigantine Geddes, and tossed her cargo of tea into the Chester River. Every Memorial Day weekend, Chestertown residents not only celebrate the event, they reenact it.

4. Fountain Park

Visit Chestertown Maryland: a beautifully ornate fountain is the centerpiece of Fountain Park.

The fountain in the center of Chestertown’s Fountain Park is nothing less than stunning. One of the earliest depictions of the fountain appeared in the 1853 edition of Godey’s Lady’s Book. It soon became associated with the style and elegance of this community. The figure of Hebe, cupbearer to the Gods on Mount Olympus, stands at the top of the fountain, pouring water. In addition to the fountain, the park is also home to summer concerts and other community events throughout the year.

5. The Shops

Walking along High Street in Chestertown, you will see all manner of great shops and art galleries. The best thing about these shops is that they are not chain stores. They are unique, locally owned businesses with strong ties to their community.

I had enough time to check out a few of them, and especially enjoyed She She on High, which is part gift shop, part DIY studio, part vintage clothing store. Literally, everywhere I looked in the store, I saw something cool, displayed beautifully.

Visit Chestertown Maryland: High Street offers many great shops, including She She on High
One of the stunning displays inside She She on High

In addition to She She on High, you can find stores specializing in beautiful art glass, Maryland theme gifts, boutique clothing, vintage finds, and so much more.

Additional Reasons to Visit

Still not convinced? Well, here are a few more reasons to consider a visit to Chestertown, Maryland.

  • The people are very friendly. You could live there 50 years or more and never be considered a local, but you will always feel welcome.

Visit Chestertown Maryland, where the parking is free and the people are friendly.

  • It’s a great day trip destination from Baltimore, Philadelphia, and/or Washington DC. Driving from any of these major cities will take right around 2 hours (slightly less for Baltimore).
  • It has a thriving art community. From galleries lining High Street to RiverArts’ special events and workshops throughout the year, you can tell that Chestertown values the arts and is dedicated to seeing them thrive in the community.

Visit Chestertown Maryland: The small town on Maryland's Eastern Shore is rich in history and also has a thriving arts community.

Have you been to Chestertown? What did you think of it? Be sure to leave a comment below and tell me!

Visit Chestertown Maryland: 5 reasons you should check out this historic town.
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5 Reasons Why You Should Visit Chestertown, Maryland
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5 Reasons Why You Should Visit Chestertown, Maryland
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Chestertown, on Maryland's Eastern Shore, is a quaint riverfront town that oozes history. Here are five wonderful reasons to make a stop there on your next Maryland road trip.
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Travelasmuch
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