Postmaster: ‘It’s time for me to go’

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Debra Chickering said she's looking forward to having the summer and Christmas Eve off. - Kyra Steck

After 42 years in the U.S. Postal Service, with 18 years as postmaster in Edgartown and seven as postmaster in Vineyard Haven, Debra Chickering retired, effective Friday.

Walking into the backroom at the Vineyard Haven Post Office, there is an immediate sense of organized chaos. Walls of stacked packages tower throughout the room, dividing it into paths and alleyways like walls of hay in a maze. Bustling employees quickly navigate through the partial barricades, searching for one name in a sea of deliveries. Leaning against the doorframe to her office, Chickering surveys the room with a quick glance, and nods in approval. After years of championing this hectic scene, of being responsible for every carrier, truck, and piece of mail in the office, she says she is ready to move on. “I really did the right thing,” Chickering said. “It’s time for me to go.”

Chickering began her career with the postal service in Providence, R.I., as a mail carrier in 1978. In 1989, she and her husband moved to Martha’s Vineyard, where they were both mail clerks — Chickering in Vineyard Haven and her husband in Edgartown. After six years, Chickering became the postmaster of Edgartown, and in 2013, the postmaster of Vineyard Haven.

In her years as postmaster of Vineyard Haven, Chickering dedicated herself to her job, working most days from 6 in the morning to 6 in the evening. She weathered the tumultuous summer months, and the even more turbulent holiday season, where she and her fellow employees would work every day from Thanksgiving until Christmas Eve. “I haven’t had a Christmas for me to stay home with my family in 42 years,” Chickering said.

Chickering, however, was happy to do the work, as she loved providing a service for her community. “I always worked on Christmas Eve because I loved being at the window, handing people their packages, because, you know, they needed them,” she said. Working on Martha’s Vineyard, Chickering said, her job was more fulfilling, as she knew the people she was serving. If she saw a package incorrectly addressed, Chickering could easily fix it and save the recipient the headache. If she saw a package meant for an elderly member of the community, Chickering would make personal home deliveries. 

“She had such a great attitude, and was always so positive,” said Matthew Montanile, who worked with Chickering for seven years. “And she worked harder than anybody.” 

Chickering’s final months at the Post Office, however, would be her most challenging. With coronavirus increasing the quantity of deliveries to the Island, and an early arrival of seasonal residents, Chickering said, they are working with three times as many packages as normal. “There is no room really for us to even move on the working floor,” Chickering said, pointing to the walls of stacked packages. “This is totally unprecedented. We’ve never gone through this before.” 

Given the increased workload and perpetual understaffing, Chickering decided she was ready to move on. Her staff, many of whom she has known and worked with for more than two decades, say they are sad to see her go. “We’ve been like a big family,” said Karen Mercier, who first met Chickering when she was a clerk in Vineyard Haven 25 years ago. “We laugh together, cry together. We had our kids together.” Jack Thompkins, a supervisor in Vineyard Haven, will be the acting postmaster, while the Post Office conducts a competitive search for Chickering’s replacement.

When asked what her future holds, Chickering laughed and said she was looking forward to taking the summer off. “I’m going to be a beach bum, that’s my plan for the summer,” she said. She is also excited to spend her first Christmas Eve at home in years: “It’s like a whole new world, a whole new chapter opening up for me. It’s like starting all over again.”