Let’s address the elephant in the room: most retirement destinations are either unaffordable or unbearable.
Chestertown, Maryland manages to be neither, offering a quality of life that doesn’t require a massive nest egg or a willingness to spend your golden years in a place that makes you question all your life choices.
Situated on Maryland’s Eastern Shore along the Chester River, this town of approximately 5,000 residents provides the rare combination of affordability, amenities, and actual charm that retirees need but rarely find.
The cost of living here runs significantly below both state and national averages, meaning your Social Security check actually covers your expenses instead of just making a small dent in them…