The next time you’re holding a donut, consider the “hole” story of its creation.

Maine sea Captain, Hanson Gregory was but a teenager, in 1847, when he noticed that donuts were usually raw in the middle. His solution? Bake them with a hole in the middle to allow more even cooking. His new donut also allowed for relaxed holding while steering the ship.

Nowadays, Hanson Gregory’s ingenuity accounts for global donut sales annually in the billions of dollars. One can appreciate that fact considering the popular, sweet treats at Anna’s Hand-Cut Donuts on West Roxbury’s Centre Street.

Maintaining its polite neighborliness for more than 60 years, the latest rendition opened under new owners Chaufan Bun and his wife, Jennifer Aing, in May, 2025. With a wide following due to its expanded menu offerings of fresh-baked donuts and muffins and a variety of tasty breakfast sandwiches, Anna’s, under Bun and Aing, seems more flavorful.

Allston-Brighton readers know that a donut baker, in order to be taken seriously, really should have Twin Donuts on the resume. That’s where Chaufan Bun baked donuts prior to opening Anna’s.

Perhaps that’s why the inviting shop quickly developed a reputation for uniquely fresh, delicious donuts. For instance, the tempting lemon donut is an irresistible powdery pillow oozing with luscious lemon. Then there is their best seller, the sinfully scrumptious honey dip. Your eyes will glaze over with each bite.

Is it any wonder customers arrive early?

The line slowly grows at 7:00 a.m. Customers – ages 2 years to 92 – know that it is worth the wait, and wait they will.

“They’ll be coming in about ten minutes,” smiles Nicole McGuire, counter person extraordinaire at Anna’s, while looking out at Centre Street. McGuire is referring to the St. Theresa School children. It’s a maroon-school-uniform tsunami of boys and girls. Wave after wave they arrive, flooding the shop with a youthful vibe. The Reddick siblings, Monroe, 9 and his sister, Presley, 6, race in.

Monroe selects a chocolate; Presley gets a chocolate frosted with rainbow sprinkles. Off they go to high-top stools, at one of two window counters.

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I take my life into my hands when I slow a rushing woman to ask her opinion. Smiling, Laura tells me that she is new to West Roxbury. “When I moved here, friends told me, ‘You have to check out Anna’s.’ I’m hooked. Do you mind keeping me anonymous?” she laughed.

“I love building relationships with the customers, seeing the regulars and meeting new faces. This is all about community,” McGuire says as she hands a gentleman his coffee.

“This coffee is the best, most consistently great-tasting coffee you can get around here,” says Tony. “I’ve been coming here for 20 years. This place is quite an improvement,” Tony smiled, then gestured toward McGuire. “You have a beautiful waitress here. It makes you happy to come here and see her smiling.”

McGuire waits, patiently, as customers ponder their orders. Their mental tennis match is underway: Should I get the honey dew cruller, coconut, Bavarian crème, coffee roll, or the audaciously delicious apple fritter?

Some order one donut, many say give me a dozen. As if selecting 12 gemstones at the Jeweler’s Building they take their time, eyeing McGuire fastidiously filling the box, “Give me four honey-dip, a chocolate, a jelly stick…”

Bun, who begins artfully hand-cutting each donut at 1:00 a.m., later occasionally appears from the kitchen, smiling as he places another treasured tray of delectable donuts on the shelf. Jennifer Aing also handles the counter, pleasantly making everyone feel at home.

Holding a jelly stick and an iced coffee, Bill O’Neill, grins, “I probably shouldn’t be in the habit, but I come here a lot.” It’s as if he’s confessing. No need. The “hole” story is donuts are good for the soul.