Chilmark has a new postmaster. Well, to call him new may be misleading, as he’s worked for the post office for 27 years. But Leigh Vanderhoop has settled into a new role, leading the up-Island postal operation as postmaster since March. Mr. Vanderhoop’s ties to the job extend beyond his own lengthy tenure at the post office. His paternal grandfather, Leonard Vanderhoop, a World War I veteran, was an Island postmaster too, operating the Aquinnah post office out of his home on Church street in the 1920s. Mr. Vanderhoop’s great-great-grandfather, William Adrian Vanderhoop, also led the Aquinnah post office in the 1870s.

“It was in their homes so they all gathered around the post office and sat around the pot belly stove and talked and then went on their way,” said local historian and genealogist June Manning. The post offices had attached stores too, where food and sundries were sold.

Mr. Vanderhoop was born and raised on Martha’s Vineyard, where his Wampanoag father and Cape Verdean mother were also born and raised. His wife was also born and raised on the Island, and the couple met at a Wampanoag tribe cookout.

Despite his family ties to the postal service, Mr. Vanderhoop’s career trajectory wasn’t linear. After high school he studied radio broadcasting at Northeast Broadcasting School in Boston, intending to pursue a career in technical communications. “I thought I would be a radio broadcaster, but I actually went and enlisted in the Army from 1981–1984,” he said. Stationed in Central America, Mr. Vanderhoop employed his education by working as a tactical communications radio operator for three years.

The army helped him transition into a career at the post office, and he began as a clerk at the Oak Bluffs post office in 1988, where he was hired by former postmaster Dickie Harris. “I worked there for a year and a half and transferred from Oak Bluffs to Chilmark as a postal clerk. That was in ’89 and I have been here ever since. All told, I have worked for the post office for 27 years.”

Mr. Vanderhoop embraces his tribal affiliations; he lives on tribal land in Aquinnah and is a tribal council member. For eight years he has overseen the operations of the tribe. “I am very integrated in the community and it’s a big part of who I am. That’s how I reach out other than through the post office,” he said.

For now, Mr. Vanderhoop has his hands full at the post office. The clerk role that he vacated to become postmaster has not yet been filled. “I basically do everything,” he said. “But I have been promised a clerk—an able body that will be ours and ours alone.” In the meantime, the Vineyard Haven and West Tisbury post offices have provided some relief.

Mr. Vanderhoop says he owes his ascension to postmaster to the support he received along the way from the community and postal service mentors. “They always encouraged me and gave me opportunities to excel and be in a situation where I could be promoted,” he said. “It’s been a good 27 years. It doesn’t feel like 27 years, but when you work the post office, it goes by quick.”