Several years ago, Jeff Hewett was at a dinner party when the subject of obituaries came up. He realized, other than being “an avid Red Sox fan” — as he’d seen in so many posthumous biographies — he wasn’t going to have much to say in his.

He didn’t have kids and worked the same job for most of his career. Another dinner guest reminded him that he could say he’s a cribbage player, but again, so are most Maine men, he said. Hewett needed something more.

An eighth-generation Mainer who’s proud of his roots, he decided he was going to visit every incorporated town and city in the state — 454, by his count — and, unlike most people who claim to have “been everywhere,” he would take a picture to prove it.

Advertisement

Hewett, 64, who lives in Cape Elizabeth, is easing into retirement from a 38-year career in printing sales that started at the Times Record in Brunswick and, in 2019, was relocated to the South Portland plant that prints the Portland Press Herald, now owned by the Maine Trust for Local News.

In embarking on his quest, Hewett didn’t map out a route to take through the state or choose a certain time or place to start. He just happened to be on Isle au Haut in the fall of 2018, on his annual hiking trip with a group of friends, when — remembering his obituary idea — he realized he probably wasn’t going to make it out to the remote island off the Midcoast again anytime soon. So, he found the town hall and asked his buddy to take a picture of him.

When they got back to the mainland, he realized he could check off Blue Hill while he was there, and Belfast, too.

“It started the ball rolling,” he said.

Advertisement

” data-medium-file=”https://i2.wp.com/www.pressherald.com/wp-content/uploads/sites/4/2026/03/image7.jpeg?ssl=1?w=300″ data-large-file=”https://i2.wp.com/www.pressherald.com/wp-content/uploads/sites/4/2026/03/image7.jpeg?ssl=1?w=640″ fifu-data-src=”https://i2.wp.com/www.pressherald.com/wp-content/uploads/sites/4/2026/03/image7.jpeg?ssl=1″ alt=”” class=”wp-image-7605572″ srcset=”https://i2.wp.com/www.pressherald.com/wp-content/uploads/sites/4/2026/03/image7.jpeg?ssl=1 640w, https://i2.wp.com/www.pressherald.com/wp-content/uploads/sites/4/2026/03/image7.jpeg?ssl=1?resize=300,225 300w, https://i2.wp.com/www.pressherald.com/wp-content/uploads/sites/4/2026/03/image7.jpeg?ssl=1?resize=600,450 600w, https://i2.wp.com/www.pressherald.com/wp-content/uploads/sites/4/2026/03/image7.jpeg?ssl=1?resize=400,300 400w, https://i2.wp.com/www.pressherald.com/wp-content/uploads/sites/4/2026/03/image7.jpeg?ssl=1?resize=200,150 200w” sizes=”(max-width: 640px) 100vw, 640px”/>

Every photo after the first one has been a selfie. Not that he hasn’t had plenty of company on his travels. There’s been his neighbor and frequent cribbage opponent Mike Drinan, who gave him a ride on his boat to Chebeague and Long islands in Casco Bay. Client-turned-friend Janet Acker did the same to Swan’s Island, off Bass Harbor. One of his hiking buddies, Ron Morrison, stuck around after a trip to make a few stops by Bangor and has accompanied Hewett elsewhere.

He’s gone by himself at times. Once, after returning from the Sugarloaf area, he realized he’d missed a town. So, one Saturday, he drove back up to New Vineyard, took a photo and went home.

“Some of them were just random. ‘Hey, we’re in Lyman; let’s find the town office,’” he said.

Most of the time, he’s been accompanied by his wife, Mary, whom he met on a blind date, though she knew him from his days bartending in the Old Port, he says, and “wanted nothing to do with me.” Their 30th anniversary is in September.

He says she partly comes along for the free lunch, the quality of which can vary depending on where they are. (They were pleasantly surprised by burgers they had in the Penobscot County town of Lincoln.)

She’s also told him that she likes just standing back and watching him talk to the people he meets wherever they are, whether it’s someone working at a town office — where he takes all his selfies, if the town has one — or giving him directions when the GPS leads to the middle of nowhere. (His car has never broken down, but he’s gotten lost plenty.)

Hewett often explains what he’s up to, which sparks a conversation. He remembers telling a woman working in a town office in northern Maine — in Allagash, he thinks — that he had come a long way to see her that day, from the Cumberland County town of Cape Elizabeth. Oh, she said, I’m from South Portland.

“Being in the business I’m in, you wind up having a connection everywhere,” he said.

He was staying with friends in Houlton when they ran into a man introduced to Hewett as Don Douglas, a member of the Maine Baseball Hall of Fame. He asked Douglas if he knew fellow hall-of-famer Bob Curry from his neck of the woods. Ah, yes, he said, the crafty left-hander.

“People know people,” Hewett said.

His “gift of gab” has helped him get rides from strangers on islands, when boats have dropped him too far from the town office to walk. There was the harbormaster on Chebeague, and the woman on Swan’s in an old Subaru, who offered to show him and his wife the prettiest beach on the island, then left them in her driveway while she went to have lunch with her brother. He flagged down a pickup truck for a ride back to his friend’s boat. When he told her what happened, she said she knew the house he was talking about; that woman was probably one of the Rockefellers.

The same skill for conversation has been essential to his career, as a liaison between commercial printing clients from all over New England and newspaper production staff. It’s also what landed him the job as the de facto tour guide for the South Portland printing plant, being one of few people who can both explain how the process works and entertain a crowd.

His travels have given him something to talk about with people back at home, too. At least a couple times a week, he said, a place he’s been will come up in conversation, when he’s asking someone where they’re from or talking about their Maine vacation. If you’re going to Washington County, he’ll tell you, Eastport has more going on than Lubec. If you’re thinking about visiting Vinalhaven, he’ll suggest you get on the ferry to North Haven instead.

Hewett outside the Quonset hut that serves as Passadumkeag’s town office. (Courtesy of Jeff Hewett)

He’ll give you an assessment of the town office there, too, from the utilitarian Quonset huts in places like Passadumkeag and the unimpressive sign on a flagpole in Ripley to the stately Queen Anne-style town hall in New Gloucester and the quaint, white clapboard building in Bowerbank on Sebec Lake.

He can show you. He’s got all the photos on his phone and in a searchable gallery on a website that his brother made for him. Flipping through them shows his thick gray hair and beard getting lighter over the six-year span. Sometimes, he’s in sunglasses or a baseball cap, others a winter hat. In the one in front of the Medford town office, he thinks he looks like a lobsterman who just returned from sea, though his tan is actually from driving with the top down on the 2006 Porsche Boxster he bought in 2020 to improve his cruising.

Hewett after a long drive to Medford. (Courtesy of Jeff Hewett)

“Do I look like I’ve had a hard day there, or what?” he said.

A few of the photos are at the signs for town lines, when he couldn’t find a municipal office, like in the Washington County town of Vanceboro. Border patrol agents there couldn’t help him either; they all live in Calais, they told him.

His final stop, at Frye Island in September of 2024, didn’t fail to deliver a tale worth recounting. He and his friend were sitting at a cafe by the ferry landing when a public works crew showed up. The dock plate was broken, and cars — like the one they decided to take over — wouldn’t be able to board the boat to Raymond until it was fixed. Fortunately, a few hours later, they were back on the mainland, his mission accomplished.

Hewett has taken plenty of day trips since then, but in more random directions now that he doesn’t have a destination to check off — to Bath in search of an electric fry pan or Parsonsfield just to go for a ride.

Although he knows about the Boothbay Harbor couple who’s been to every Maine post office, he hasn’t heard of anyone else who’s visited every town.

As he cuts back on his work week, he plans to start tackling the state’s 28 or so plantations, most in far-flung places. He’s looking forward to revisiting Aroostook County and to his first trip to Matinicus, an island 20 miles out to sea.

It will give him something to do with his newfound free time, and something else to say.