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Roger Guest strolls the lawns, where airplanes (Cub, foreground; Citabria, background) rather than cars rule. (Caroline Sheen)

A Walk in the Airpark

Rest and renewal in a long-standing pilot community.

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His daughter, Annette Lerner, recalls that he turned down a proposal by CNN to do a segment on his continuing to fly into his 90s. “If the FAA finds out this old codger is flying at 91, they are going to take my license away,” Morris told her. He kept on flying. In 2005, he made his last solo flight. It was his 98th birthday.

He died a few months later.

“He didn’t have grand visions, and Kentmorr was what he hoped it would turn out to be,” Lerner says. “To my dad, it was always about the airplanes and airplane lovers.”


For Years, After taking a ferry or crossing the new four-mile-long Chesapeake Bay Bridge, visitors bound for Kentmorr had to navigate winding and sloppy dirt roads. In recent decades, the roads were paved, and commuters and retirees began to settle in the relatively inexpensive housing. Since 1950, the island has grown from about 2,000 residents to 16,000. Kentmorr saw its biggest expansion in the late 1970s and 1980s, when a group of retiring pilots and their families joined the neighborhood. The residents were close then, friends lured to Kentmorr by other friends. They helped one another build hangars and houses and airplanes. They stayed into old age.

When Jim Cannon died in 1994, his friends Roger Guest and Bob Martin scattered his ashes over the runway from Martin’s Fairchild 24. When Martin grew too weak to hop into the cockpit, Guest flew Martin’s Piper Cub around the traffic pattern so Martin could watch it fly. When Martin died in 1999, Guest and another friend scattered Martin’s ashes over the runway too.

“We care about the place,” says Guest, 74, who moved into Kentmorr in 1987 (and, when he was the airport manager, extended the runway). “It’s our home. Bob loved this place. It was just one group, especially that early group, and we lived on like a family compound.”


In recent years, housing prices have crept up and a new generation of pilots has moved in—wealthier ones who still work and can afford to have two homes: one near their workplace and the other a weekend getaway on a grass strip.

Mike Ashford, who spends most of his time at a home in Annapolis near his 100-employee restaurant, bought Morris’ place in 2006. Vince Massimini, 61, bought his place in 2000 after spotting a for-sale sign while making a proverbial $100 hamburger run to the Kentmorr restaurant with his wife, Pat. They split time between Kentmorr and a condo near Washington, D.C.

Two years ago, Paul Howey, 56, and his wife, Christiane, 55, bought the old Martin place and are rebuilding its rotted hangar. The owner of a tech company in Columbia, Maryland, Howey spends most of his days at his home in Ellicott City, a suburb of Baltimore.

The demographic changes have created two distinct groups in the neighborhood and they rarely mingle. Longtime residents look askance at their newer neighbors, who aren’t around all that much. “It would be nice if they were here year-round,” says Peg Cannon, Jim’s widow. And the weekend pilots would like to see some new blood in the neighborhood to get more airplanes flying.

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