The raised doughnuts at Donuts With a Difference are light and airy and great for the eater who’s looking to take down two or three, but the best thing on its menu is the humble chocolate frosted cake. It’s dressed up a bit with chocolate sprinkles, and its exterior is crispy and perfectly fried without holding onto the taste of fry oil, which is a problem that too frequently plagues cake doughnuts.

A-Town, represent. At Gail Ann Coffee Shop, doughnuts go for just $1.65. Best bets: chocolate glazed or the jelly. (Note: Gail Ann’s is closed for summer 2021 vacation from July 10 to 25.)

Donut Villa Diner is a full-service breakfast-and-lunch joint, but “donut” is in the name for a reason. This doughnut-filled diner — which expanded to Cambridge in June 2021 — offers a variety of flavors (including some gluten-free and vegan options). While the classic honey dip is Donut Villa’s bestseller, doughnut enthusiasts should be sure to try the powdered doughnut stuffed with lemon cream or the Nutella-filled doughnut with chocolate glaze and hazelnuts. Donut Villa also serves dishes made with doughnuts, such as a cheeseburger with a doughnut instead of a bun and a doughnut Benedict. 

A relatively new addition to Arlington, Mass Hole Donuts sells — you guessed it — doughnut holes (and only doughnut holes). The flavors change weekly and often pay tribute to local towns, landmarks, and themes. There’s the Peabody Peach Party, for example: a brioche hole dipped in a peach and honey glaze, topped with a spiced cinnamon drizzle. Or try the Masshole Tea Party, a classic cake hole in a milk tea-infused glaze, topped with caramel drizzle and vanilla teacake crumbs.

Union Square Donuts in Somerville (and now in the Boston Public Market, Time Out Market Boston, and Brookline) is a doughnut shop of a different breed. Instead of having a plain old bakery display case — utilitarian furnishing is typical to old-school doughnuts shops — Union Square Donuts’s shops are furnished with fancy espresso machines and tables and countertops crafted by someone who cares about wood. Don’t let the hipster facade deter you; these are some of the best doughnuts you’ll ever eat. The brown butter hazelnut crunch is a treat, but Union Square’s doughnut magnum opus is its maple bacon. The flavor combination is a borderline cliché at this point — seemingly every cool doughnut shop from Portland, Oregon, to Portland, Maine, has a maple bacon situation — but it doesn’t matter because it’s perfect.

The original Kane’s is in Saugus. It’s perhaps most famous for making coffee rolls the size of bowling balls, but its doughnuts aren’t half bad either. After six decades of operation in Saugus, Kane’s decided to expand to Boston in 2014. When that happened, every doughnut-loving Bostonian got a little luckier. Honestly, everything on the menu is worth trying. And a note for the coffee snobs: Kane’s uses beans from Atomic Coffee Roasters in Beverly.

Twin Donuts possesses one of the very best facades in all of Boston, but it’s more than just a pretty storefront: Twin is also serving some very solid doughnuts. And for $1.25, they might be the cheapest in the city. The classic honey dipped never disappoints, but if Twin’s got chocolate butternut — which is a rarity — be sure to grab one of those, too. Twin is also an excellent spot for a cheap greasy spoon-style breakfast.

Blackbird Doughnuts in Boston’s South End (and also Beacon Hill, Brighton, Fenway, Harvard Square, and Newton Centre) is, it has to be said, now iconic. It’s slinging some of the city’s most excellent doughnuts. The salted toffee is perfectly balanced and should be part of your dozen, but the signature flavor — a vanilla bean old fashioned with vanilla bean glaze — is what keeps the lights on. Also worth your pennies: something savory from Sally’s Sandwiches, which is located inside the original shop on Tremont Street. (Note: The Harvard Square location is temporarily closed but expected to reopen in September 2021.)

Mike’s Donuts has been a staple of Mission Hill since the 1950s. A fresh, hot honey dipped from Mike’s is tough to beat, citywide. Bonus: Whenever you order multiple doughnuts, Mike’s employees include a couple of doughnut holes on the house.

From local pastry chef Kate Holowchik — an alum of Yvonne’s, the Townshend, and more — the Lionheart Confections pop-up has been amassing a cult following during its frequent 2021 pop-ups in and around Boston. Catch Lionheart, with its ever-changing menu of whimsical doughnuts, at its Reign Drink Lab residency throughout summer 2021; it’s appearing there every weekend. (Watch Instagram for updates, flavors, and other special events, and stay tuned for news of a permanent location.) If the ube cinnamon roll is available, definitely get it.

Anna’s is as old-fashioned as it gets, with a purple formica counter and circular swivel stools upholstered with cracked black vinyl and bolted to the tile floor. Get a jelly here.