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Secluded Smith Island Is Living at Its Best Talk about hometown pride! When I asked a grizzled waterman who lives on Smith Island, Maryland, if he’d like to accompany me to one of the community’s other nearby villages, he replied “Nope, I’ve already been there.” While the twinkle in his eyes suggested he wasn’t completely serious, the fact is that residents of Smith Island in the Chesapeake Bay good-naturedly tout the superiority of their tiny town over the other two. Along with being loyal to the little village where they live, Smith Islanders are hardy, independent, and welcoming to visitors.