Kam Ali stops at Eighty 8 Donuts while leading a donut tour in the Old Port. Ali is working for The Maine Donut Tour this summer, leading groups around the city and lending his knowledge of local architecture, history and Portland’s food scene, all while stopping for donuts. Derek Davis/Staff Photographer

Kris McClure opens his Maine Donut Tour talks with a point of pride that surprises tour goers and partly justifies his new business launch, if justification were needed to feed visitors some of the city’s best doughnuts on an educational stroll through the Old Port.

“Maine actually invented the doughnut,” he told the five people gathered on the corner of Fore and Exchange streets on a recent Friday morning for the start of his 90-minute walking tour that blends local history with doughnut discussion, along with stops for samples at The Holy Donut, Eighty 8 Donuts and Hifi Donuts. McClure launches into the lore, familiar to many Mainers, of how ship captain and Rockland native Hans Gregory modified his mother’s spiced fried dough to form the ring-shaped doughnut we know today.

Gregory’s mother, Elizabeth, put hazelnuts or walnuts in the center of the dough, and thus called them doughnuts. But the nuts kept the middle of the dough from fully cooking, leaving it gummy and raw. McClure tells his tour group how Captain Gregory is said to have impaled a doughnut on a spoke handle of his ship’s wheel because he needed his hands free to steer in a storm. It’s by far the most entertaining doughnut origin story, with Gregory both jettisoning the undercooked center and inventing the doughnut hole in one swift motion.

But as McClure duly noted, and food historians tend to agree, the actual invention of the doughnut hole likely involved a crude pastry cutter, a story Gregory himself shared with the Washington Post in 1916.

“I got an inspiration, a great inspiration,” Gregory is quoted saying in the Post story. “I took the cover off the ship’s tin pepper box and I cut into the middle of that doughnut the first hole ever seen by mortal eyes!”

The Post then asked if Gregory was pleased by his innovation. “Was Columbus pleased? Well, sir, them doughnuts was the finest I ever tasted. No more indigestion – no more greasy sinkers – but just well-done fried-through doughnuts.”


Confirming the authenticity of old food legends is tricky business, and so McClure smartly hedged and moved on. “A few more people want to claim they invented the donut, but we’re sticking with that for today,” he said before leading the group down Wharf Street’s cobblestones to its first stop at The Holy Donut in its relatively new home on Commercial Street.


To preface the morning’s tastings, McClure told the group how he built the tour around three independent specialty doughnut shops, with the aim of supporting local business and giving visitors a sweet taste of the city. “It’s absolutely insane that these three amazing doughnut shops exist within a mile of each other,” McClure told the tour, sincere awe in his voice. “These doughnuts, to me, are an experience. Always. Sometimes I go to a restaurant and spend $100 or maybe $200, and it wasn’t always a great experience.”

Jess Yeomans, a resident of South Portland and self-proclaimed doughnut fanatic, tries a dark chocolate sea salt donut from The Holy Donut while in the Old Port with Maine Donut Tour. Derek Davis/Staff Photographer

What supports McClure’s take is that the three Portland shops offer distinctly different styles of doughnut. With its recipes born in founder Leigh Kellis’ kitchen in Munjoy Hill 12 years ago, the Holy Donut features Maine potato donuts, made with mashed potato that has been passed through a ricer to give it airy, fluffy texture that keeps the donuts from being dense. Eighty 8 Donuts on Federal Street specializes in bite-size donuts with fun, outside-the-box flavors and toppings like crispy Fruity Pebbles cereal on their Bamm Bamm doughnut and crushed Oreos on the Cookies ‘n Cream doughnuts. And Monument Square’s Hifi Donuts prides itself on “old-world style” doughnuts with crisp, lightly crunchy exteriors and luscious crackly glazes.

“It’s amazing how ingenious people in this town are, finding potential in food niches like doughnuts,” said Lynn Tillotson, president and CEO of Visit Portland.

Tillotson said walking food tours are a natural fit for an eminently walkable city like Portland that hosts loads of must-try restaurants and food businesses in a relatively small area. “And because we are a culinary destination, for people to get the lowdown on local food from a local tour guide’s perspective, it gives them an insider’s perspective, and a deep dive into the subject.”


A Lisbon Falls native – home of Moxie soda, he proudly tells tours – McClure, 41, has worked in the tourism industry for 10 years. In 2017, he and friend Khaled Habash bought Maine Duck Tours, and McClure gave amphibious tours of the city until he left the business last winter.

In February, McClure was brainstorming with Kevin Ouellette, owner of Maine Souvenir Shop, about a new food tour for Portland, one that would both help local businesses and lure visitors with a tempting food niche. Portland has hosted walking food tours for more than a decade, starting with Maine Foodie Tours in 2009. That business is now known as Maine Day Ventures, which offers multiple tour options, including some targeting specific neighborhoods, such as the East End, or specific food types, like seafood.

As McClure researched possibilities, he discovered the Underground Donut Tour, a walking tour started four years ago featuring four doughnut shops in downtown Chicago. The business became successful enough to launch tours in eight more cities, including Boston.

But McClure is an experienced tour operator and guide, built tall and lean with a bicyclist’s legs, perfect for urban hiking to burn carbs. And he had no problem selling the concept to the doughnut shop owners.

Ali holds a box of varieties from Eighty 8 Donuts for Yeomans.  Derek Davis/Staff Photographer

“It’s a great idea, and we wanted to get behind it and support it as much as we can,” said Garrett Champlin. He and his partner, Ellen O’Keefe, opened Eighty 8 Donuts on Federal Street last year after several years operating as a food truck. Champlin said it was a no-brainer to participate in the Maine Donut Tour.

“They do all the legwork, and we just supply the doughnuts,” he said.



“Our approach to the shops was about celebrating them and partnering with them in a way that makes it a win-win for everyone with as little disruption to their business as possible,” McClure said, explaining that funds from the $40 doughnut tour tickets cover the cost of tasting samples for tours. The arrangement has McClure notifying the shops when his tour group will be arriving and how many people will need samples, and it allows them to skip lines for their goodies, a real boon since his tours now run twice a day, at 9:30 a.m. and 11:15 a.m., often busy times for local doughnut stores.

“Food tours are like orchestrating a Broadway show every day,” said Pam Laskey, owner of Maine Day Ventures. She claps her hands stage manager-style. “Places, places everybody!”

“Coming out of operating a tour bus that goes in and out of the ocean six days a week, a donut tour is a world apart in terms of logistics,” McClure said.

After swooning over Dark Chocolate Sea Salt doughnuts from The Holy Donut, McClure’s tour group heads down Long Wharf for a little show and tell on the city’s fishing industry. He gives a wave and playful shout to a nearby tour guide leading a group for Portland By Foot. As McClure leads his group back uphill through Old Port, a duck boat passes. Prompted by the Maine Duck Tour guide, the duck boat people quack at the doughnut group.

“We want to be more of a doughnut tour than a history tour, because there’s a lot of great historical tour options in Portland already,” McClure said. He works ample history into the 90-minute walk, including the Portland’s unfortunate history with fires and its establishment as a major port city, as well as fun exercises like finding the Revolutionary War cannonball set in the side of the Colesworthy Building on Exchange Street. But he doesn’t bombard tour goers with historical facts and trivia, instead giving them the chance to take in the lovely Old Port architecture and talk donuts along the way.


At Eighty 8 Donuts, Champlin wows the crowd with fresh, warm Bamm Bamm and Cookies ‘n Cream doughnuts. Hifi Donuts, the last stop on the tour, served up a glazed Hifi Cruller, golden and crisp outside, light and airy within, along with an old-fashioned doughnut with wild green cherry frosting flavored subtly with vanilla and tarragon.

“I was surprised there are enough doughnut shops in town, and enough different styles of doughnuts, to have a doughnut tour,” said Jamie Pacheco of Auburn. Tour goers said they were also happy to find that they didn’t waddle away from the tour ready for a nap. While people are free to eat more, McClure doles out bite-size portions on the tour so nobody feels overstuffed.

Since launching in April, the Maine Donut Tour has run two tours each morning from Thursday through Sunday, with tickets available for purchase on its website. McClure said he expects later in the summer to add tours Monday through Wednesday as well.

“The city of Portland and the amazing doughnuts here sell themselves,” McClure reasoned. “It’s up to us to screw it up.”

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