Tilghman Island is best described as an “old-fashioned waterman’s community.” It is located on the westernmost tip of the county, and it is a popular place to live for those involved in the seafood business. It’s also a popular destination for those interested in fishing trips and other water adventures.

Many people choose to buy a second home in Tilghman because of the privacy and fantastic Chesapeake Bay views found on the island. The island is home to an oyster preserve and a few shops and restaurants. (Try my favorite, Two if by Sea.) Tilghman also has easy access to more amenities in nearby St. Michaels.