Discover Coastal Dream Towns

After canvassing all coasts for towns with seaside charm, a lively beach culture, and good housing, these are our top spots for planning quick trips or finding a new place to live.

Dream Towns

Plan a vacation location or find a new place to call home in this roundup of our favorite coastal communities.

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College Community

College Community

Chestertown, Maryland

Chestertown, a charming Eastern Shore village on an arm of the bay, is bounded on one side by the Chester River and otherwise surrounded by farm fields and even smaller hamlets. Exquisitely restored Colonial homes line the brick-paved sidewalks and oak-shaded streets. Home to Washington College, here a wealthy older generation lives along side a vibrant college community.

Find out more about Chestertown, Maryland


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