By Charlie Pike
Photos by Nicole Wolf
Styled by Catrine Kelty
From our March 2025 issue
There’s a modest plaque on a slab of stone off Old County Road in Rockport, in the yard of what is now the Nativity Lutheran Church. “In Commemoration,” it begins, in capital letters. “This is the birthplace of Captain Hanson Gregory, who first invented the hole in the doughnut in the year 1847. Erected by his friends Oct. 31, 1947.” At its dedication, the Rockland Courier-Gazette reported, spectators sang a patriotic tune, ate freshly fried dough, drank cider, and made merry in memory of the hole-in-the-doughnut founding father.
Hanson Crockett Gregory was born into a prominent shipping family in either 1831, as he told multiple reporters, or 1832, as his gravestone has it. He first went to sea as a teenager, in 1845, working as a mate and a cook and worked his way up through the ranks to become a captain. According to one account, he was decorated by Queen Isabella of Spain for rescuing shipwrecked Spanish sailors. What he is most remembered for, though, is the doughnut.
How exactly he came up with the idea to cut a hole in the middle of fried dough remains foggy. At the turn of the century, Gregory was quoted in the Boston Post and Washington Post explaining that he first used a tin pepper box to cut a hole in the undercooked middle of some fried dough in 1847. Later, he told the Boston Evening Record that he used a biscuit cutter. “The idea spread like wildfire,” he added. In a 1952 self-published pamphlet titled “Who Put the Hole in the Doughnut,” Fred E. Crockett, Gregory’s second cousin, asserted that Gregory invented the hole at age 15, in the kitchen, after noticing the centers of his mother’s fry cakes were soggy. “I have an idea,” Gregory supposedly told his mother, before picking up a fork and making a historic poke. At the plaque’s dedication ceremony, this was the story that was told.
Versions of the tale don’t stop there. Another, the most apocryphal of them all, holds that while navigating through a thrashing storm, Gregory stabbed a piece of fried dough he was eating onto a spoke of the ship’s wheel so that he could navigate with both hands. “I don’t know if you’ve seen a ship’s wheel lately,” says Sandy Oliver, a writer and researcher who lives on Islesboro and has been studying New England’s food history for half a century. “If you took your average dough and you smashed it [on one of the spokes], what you’d have is a pile of crumbs when you’re all done.”
Oliver has a particular interest in maritime diets, poring over diaries, letters, account books, and other seafaring records to understand what people used to eat. “Almost nothing is invented with food,” she says. Rather, incremental development is the overarching narrative — constant adoption and adaptation. Humans have been frying dough for thousands of years. The Old Testament’s book of Leviticus mentions offerings of “fine flour with oil.” In China, the practice produced youtiao. In East Africa, mandazi. Mexico has churros, while Mongolia has boortsog. In the 17th- and 18th-century Netherlands, olykoeks were the ascendant fried dough, and that’s where histories of the modern American doughnut often begin.
Dutch colonists brought their hole-less “oil cakes” to New York (née New Amsterdam), and fried dough quickly migrated up and down the Eastern Seaboard. On 19th-century whaling vessels, crews would celebrate their 1,000th barrel of oil with a feast of fried dough. By 1846, at least one cookbook was advising putting holes into fried cakes. And yet, it was Maine’s Captain Gregory who was deemed the official inventor of the hole at the first annual convention, in 1941, of the National Dunking Association, a semi-serious industry group that fused commerce and culture in an effort to popularize doughnuts and instruct in proper dunking technique, with leadership over the years that included Jack Lemmon, Red Skelton, and Johnny Carson. In a debate for the conventioneers’ support, Fred Crockett, the Gregory relative, beat a Wampanoag chief, High Eagle, who argued that the hole was invented by an ancestor whose arrow, straying from its intended target, a Puritan housewife, pierced a nearby flat cake. Thus, Maine became the birthplace of the doughnut.
The sign above the door of Village Donut & Bakery, in Raymond, says thanks for 10 years of business. They’ve been open 12. “Ah, my friend is here!” the guy behind the counter said when I entered at 7:30 one morning. Confused, I gave something like a both-arms-raised cheer. I’d never been there before (but soon learned that every first-time customer gets a free doughnut). The shop would be the first of 22 I’d visit across Maine over the course of a month, on a sugar-crazed blitz in pursuit of a better understanding of our state’s present-day relationship to doughnuts.
Before I could order, the Village Donut employee asked if I was the carpet guy. I told him I was writing a story about doughnuts. “You should talk to this guy!” he responded, pointing out a man in a Vietnam Veteran hat having breakfast at a nearby table. “He was around when the doughnut was invented!” The Vietnam vet smiled and, unprompted, launched into the Captain Hanson Gregory story, opting for the version with the spoke of a ship’s wheel piercing the fried dough. “They used to teach us that story in school,” the woman he was eating with chimed in.
Broadly speaking, there are two types of doughnuts nowadays, cake and yeast, the former risen with baking powder or baking soda, the latter risen with baker’s yeast. Cake doughnuts are relatively moist, dense, and a little crumbly — think old-fashioned or cider doughnuts — relative to the airier yeast doughnuts. Some shops devote themselves to one or the other, but many, like the Village Donut, do both. The cashier told me workers from the Dunkin’ across the street come in to get their doughnuts (Maine, in addition to its many independent doughnut shops, has the fifth most Dunkin’ locations per capita in the country).
I ordered a couple of yeasts. The raised sugar is a classic, light but chewy doughnut sprinkled with granular bits of sugar. The Boston cream had a silky, rich vanilla-custard filling that felt right on a cold, gray morning. In fact, the whole shop, with its aroma of oil and sugar, pour-your-own coffee station, and abundant conversation, felt like a refuge. Traveling around the state to eat copious quantities of fried dough, I found a similar atmosphere at other mom-and-pop shops. At the Donut Hole Cafe, in Buxton, I blew on my coffee, and the solicitous cashier was quick to ask if it was too hot and if he could get me an ice cube. The glazed blueberry cake doughnut, by the way, was a hearty and subtly sweet delight.
At the County Bakery & Grill, in Mars Hill, a note was taped to the door: “Please Wait, Be Back in 10 Mins.” Shortly, owner and baker Rosemary Lavway, all smiles, pulled up and popped open the door for me and another customer. The man bought brown bread. I got buttermilk doughnuts. Lavway makes them like her grandmother did and said they once made an old man cry. “I haven’t had doughnuts like this since my grandmother made them!” he told her.
The Cookie Jar, a mainstay in Cape Elizabeth, has been around since the 1950s and sticks to a lineup of classic glazed and frosted doughnuts. The glazed chocolate cake was almost as fudgily decadent as brownie batter. Elaine’s Bakery, in the sleepy little town of Milo, delivers doughnuts all across northern and central Maine. And Congdon’s, in Wells, has become a major destination for doughnut lovers over the course of its 70 years in business. The chocolate-frosted yeast doughnut just about melts in the mouth.
At Dough Boys, in Limerick, I wound up chatting with a guy in a Limerick Transmission shirt, a deliveryman for Brackett’s Orchards, the cashier, and a woman named Sue, whose son makes the doughnuts. I brought up the story of Captain Gregory. “But it’s disputed,” I concluded. “Everything’s disputed,” said the man in the Limerick Transmission shirt. “Mainers have been known to tell a story.” Then, he told us about how he and some friends used to catch the Dough Boys baker on their way to go fishing early in the morning, before the shop opened. The baker would give them a box of fresh doughnuts. “Steamin’,” he recalled.
At Dough Boys, I ordered a honey-glazed yeast doughnut and a glazed cider. The cider doughnut was soft and sugary, with a perfect crumble. Alex Schwartz (who uses they/them pronouns) could probably describe it better. Diehard doughnut aficionados do exist, and Schwartz is one of Maine’s foremost. A Bath resident, they review cider doughnuts on Instagram, in addition to managing the New England Cider Donut Map, a Google Maps resource marking more than 250 farms, orchards, and stores that dish out cider doughnuts throughout the region.
Early in the pandemic, Schwartz would escape the claustrophobia of the Boston area, where they were living, by going on hikes around New England, often seeking out a treat to cap off an excursion, especially cider doughnuts, although they often proved elusive. “Someone should make a resource that locates where you are and then tells you if you’re near some kind of place that sells them,” Schwartz thought. With a background in video-game development, they figured it wouldn’t be much of a technical challenge.
“It kind of started as a bit,” Schwartz says. The map took off after they asked users on Reddit for help locating purveyors of cider doughnuts. “People had this almost religious affiliation to the place that they grew up and the doughnuts that they had from their childhood,” says Schwartz, who decided to cultivate the hammy persona of a connoisseur and food critic (their Instagram handle is “ciderdonuteur”). “I’d be like, the texture of the crumb of this one has a moistness and denseness that really notes forward of oak.”
But along the way, Schwartz really did wind up learning a lot about doughnuts. Soon, NPR invited them to do a cider-doughnut tasting, morning news shows reached out, and the Boston Globe chronicled their doughnut explorations. “I started getting calls,” Schwartz says, “and they’re like, ‘Well, you’re the expert. You need to tell us what the best is.’” Being a donuteur was no longer just a gag.
For Schwartz, a great cider doughnut is half about quality, half about experience, and their favorite in Maine is from Thompson’s Orchard, in New Gloucester. “The taste was a 10,” they explain. Schwartz likes that even though it’s a cake doughnut, it has a crispness and lightness to it. Plus, the orchard sits among rolling hills, always seems to attract friendly people, and has those photo stand-ins — the life-size cutouts you can stick your face through to become, say, a baseball player. “They hit on all the things for a Saturday with the family,” Schwartz says.
In 2023, Schwartz’s doughnut expertise landed them a speaking engagement at the inaugural Rockport Donut Festival, along with Alexis Iammarino, an artist, codirector of Thomaston’s Interloc art space, and fellow doughnut fanatic. The festival brings in a number of doughnut makers and also offers, among other things, live music, a 5k race (not a bad idea before binging doughnuts), a parade, and a keynote address on doughnuts, which Iammarino presented the past two years.
Iammarino first encountered Maine’s doughnut mythology in 2014, while working on a mural at the Flanagan Community Center, in Rockland. During a visit with the Rockland Historical Society, someone mentioned Captain Hanson Gregory. Curious about the story — and respectful of the local pride taken in this claim to culinary fame — Iammarino recruited artists to make works inspired by the invention of the doughnut. The results ranged from Renaissance-esque oil paintings of jelly doughnuts to a diorama depicting a sea captain eyeing a giant vanilla-frosted doughnut through a spyglass. The resulting works came together in a 2016 exhibit, Hole History: Origins of the American Style Donut, mounted at a pair of galleries in Rockland. “My idea was that artists from all over the country, and in this case, the world, would weigh in on the idea that a 19th-century sea captain invented [the modern doughnut] as a teenager,” Iammarino says. “The doughnut sort of becomes the standing symbol for the adjective of what it is to be American.” Since then, she has put on three more variations of the show.
Iammarino also compiled an exhibition catalog that incorporated old press clippings and essays about doughnuts and doughnut history. In an essay titled “Love, Loathing, and Doughnuts,” Sandy Oliver, the food historian, ruminated on the international history of fried dough. “Maybe doughnuts aren’t all-American, but their ubiquity is,” she wrote, noting that fried pastries have often been regarded as an indulgence, used to mark special occasions. “Where else in the world, though, would we find people eating festival food daily than in prosperous America, a kind of promised land for the globe’s downtrodden?”
Where else in America would we expect to find a doughnut-hole-inventing sea captain than in Maine, with its aura of self-sufficiency and long history of clever tinkering? After all, Mainers have also invented or improved upon everything from earmuffs to caterpillar treads to chewing gum to sewing machines. Hard work can be a worthy end unto itself, as Todd Bross knows. Bross is the owner (or, as he prefers it, chief frying officer) of Ruckus doughnuts, in Rockland. He goes to bed in the midafternoon and gets up just after midnight, when he heads to the Ruckus kitchen. For the most recent doughnut festival in Rockport, during 19 straight hours of production time, Bross and his team made more than 1,300 doughnuts. He didn’t get anything more than a quick nap for two and a half days. “I’ve always loved doughnuts,” Bross says.
His passion traces back to elementary school when, after a four-night run as Santa Claus in a Christmas musical, his mom rewarded him with two dozen chocolate-filled, powdered-sugared Dunkin’ doughnuts, at his request. These days, his favorite doughnut is his own: a yeast doughnut right out of the fryer, at about 5 a.m., no toppings, no glaze — just a doughnut in its purest form. But doughnuts have been trending toward maximalism in recent years, especially at newer shops, and Ruckus, which got started in 2021, is no exception: doughnuts decked out with candy crumbs, dolloped with various creams, filled with mousses. Glazes in flavors like mascarpone-espresso or lemon-poppyseed. Maybe that’s another thing that makes doughnuts so very American, the relentless revision they undergo. (Remember the cronut craze of 2013? No surprise that a French baker introduced the hybrid croissant-doughnut in New York, not in Paris.)
MeMe G’s, in Old Town, serves up made-to-order doughnuts that, at about five inches in diameter, are sized more like a personal pizza than a typical doughnut. Flavors are named after people around town. “Do you like sugar?” owner Cory Thibodeau asked me, pointing to the Tasmanian Terrill Walkoff, named for his kid’s friend who hit a walk-off homer in the final game of the Little League season last year. “You’re gonna have to sign a waiver if you plan to drive after.” The doughnut was covered in chocolate frosting, brownie bits, cookie dough, and peanut-butter cups.
Meanwhile, since 2012, Leigh Kellis’s contribution to the ever-evolving doughnut scene has been to repopularize the use of potato as an ingredient, a Yankee tradition that has roots in the ample availability and affordability of one of Maine’s staple crops. Kellis founded the Holy Donut in Portland — there are also locations in Brunswick, Scarborough, and Arundel now — with a doughnut recipe that calls for Maine russets to be shredded into little rice-like grains and mixed in with flour. The result is a moist, spongy doughnut with a crackling edge.
Options for people with dietary restrictions have been growing too. The Donut Grove, in Orono, nestled between a laundromat and a grocery store, sells only vegan doughnuts. Founded by a nurse and a teacher, the shop has been open for a year, with offerings that range from classic (a potato doughnut with cinnamon and sugar) to avant-garde (grape-filled with peanut-butter glaze). A few miles away, in Veazie, Raegamuffin’s Gluten Free Bakery makes a cinnamon-sugar cake doughnut that I would never have guessed was gluten free. Quite a few establishments that make regular doughnuts now provide some gluten-free alternatives. Down in Kittery, Lovebirds does doughnuts that are vegan, as well as doughnuts that are gluten-free and vegan. The vegan chocolate-ganache-dipped with sprinkles immediately became a personal favorite.
Variations on the doughnut seemingly know no bounds, even just within state limits. At Enzo Benzo Specialty Donuts, in Eliot, the owner made me a doughnut with pistachio cream piped into it — nutty, light, not too sweet — and another with cannoli filling. I stopped in right before the holidays and found a group of dentists doing a white-elephant gift exchange inside. “Our manager loves this place,” one of them told me. “Someone drove a car through our practice, so we haven’t been working for about a week now.” Such is the solace doughnuts can provide. Though Enzo Benzo does offer some hole-in-middle doughnuts, the specialties are those filled ones, inspired by Italy’s bomboloni. If our criteria for doughnut-hood derives from the Captain Gregory story, are these hole-less Italian-style doughnuts oxymoronic? Anyway, they were tasty enough that I wasn’t inclined to pursue the question.
Other stops on my doughnut tour of Maine: Old Time Donuts, in Damariscotta, which makes a mean old-fashioned doughnut; 115-year-old Reilly’s Bakery, in Biddeford, which serves a solid chocolate frosted; a trio of stalwart traditional joints in the Lewiston-Auburn area — the Italian Bakery, Labadie’s Bakery, and Georgio’s Pizza & Donut Shop, the latter’s Boston-cream doughnut causing me to exclaim, alone in my car, “Oh my god!”; the Only Donut, in Belfast, which makes a picture-perfect, Simpsons-inspired strawberry-frosted and rainbow-sprinkled doughnut called The Homer; and the Eighty 8 Donut Cafe, in Portland, where artistically and liberally topped mini doughnuts are fried to order.
At Lil’s, a cafe and bakery in Kitt-ery, the house specialty is crullers. Crispy on the outside, airy and eggy on the inside, these turned out to be my absolute favorite bites in all of my doughnut touring. They reminded me of the thin, crepe-like pancakes my grandmother used to make. And yet, the French cruller, like the Italian bomboloni, probably runs afoul of a strict sense of the American doughnut. Whereas Captain Gregory instructed us to cut a hole, a cruller’s hole comes from extruding the dough into rings — no cutting required.
So my favorite doughnut might not be a doughnut at all, and alas, the National Dunking Association is no longer around to weigh in. But on the other hand, maybe it’s only fitting that, in the purported birthplace of this most American of pastries, we should take a more inclusive view, welcoming influences new and old, from near and far. What could be more American than that?
We asked the Down East staff about their favorite Maine doughnuts. Check out what they said here.
