JOHN HOCKENBERRY had read about Smith Island years ago. It sounded almost mythical: the only inhabited Chesapeake Bay island in Maryland that is not connected to the mainland. He finally got there three years ago, and after just one visit, he took a leap of faith and paid $120,000 for a second home — a two-story house built in 1900.

Since then, he has found that Smith’s slower pace, its remoteness and its people suit him and his family.

“It’s become a part of our life, with our children, our extended family,” said Mr. Hockenberry, a real estate broker who lives in West Chester, Pa. “We kayak, we fish. We crab, of course. There’s so much to do down there if you like the outdoor life.”

The Hockenberrys are monthly weekenders in summer and visit less often in other seasons, but he said the warmth of the islanders, no matter the season, always makes him feel more than welcome. “It’s nice to know there are still communities like that around,” he said....