Prince of Darkness at Staccato Gelato
Naturally, Staccato Gelato deals primarily with its namesake frozen dessert. But Friday, Saturday, and Sunday mornings, their house baker whips up an array of cake doughnuts, some good (maple-glazed and cardamom-dusted), some bad (the ginger doughnut tastes like a pine tree, and the Guinness tastes like stale beer). The Prince of Darkness may not be as out-there as some of its brethren, but it offers the best balance of Staccato's myriad options. A crunchy shell gives way to a crumbly interior tasting of fudge brownies, and the best part, it isn't even remotely too sweet. The devil approves.
Old-Fashioned Glazed at Helen Bernhard Bakery
A Portland establishment since 1924, Helen Bernhard Bakery feels like it's in an entirely different era from the present. Whether it's the mob of smiling old ladies behind the curved glass showcases or the prices-from-another-economy (69 cents for a doughnut? What is this, Safeway?), this place recalls a more innocent era, when people were perhaps a little less inclined to turn their noses up at a sugar-and-carb bomb. The bakery's old-fashioned glazed is the platonic ideal of the form, with a crisp crust and perfectly balanced not-too-sweet not-too-thick glaze giving way to a dense cake with just a hint of buttermilk sourness.
Potato Doughnut at Fleur De Lis Bakery
This popular Hollywood-district side-street bakery puts out one of the best sourdough baguettes in Portland, and, for those rising early enough on a Saturday or Sunday and patient enough to withstand the lines streaming from the cash register, a few killer doughnuts. While the raised doughnuts are a superlative example of airy heaven, the potato doughnut ratchets the indulgence further with a more dense cake base dusted in cinnamon and sugar. An added bonus: they give you the doughnut hole, too!
Raspberry-Filled Doughnut Holes from Grüner
"Alpine-inspired" restaurant Grüner changes up its doughnut selection on a whim, but no matter what's on the current menu, you'll get something leaps and bounds better than the stale rings of dough sold at most establishments. Of all the ones we've tried here, we still think the raspberry-filled, powdered sugar-dusted doughnut holes are the best. These inch-and-a-half-thick spheres hide a core of bright raspberry jam and release a mouthwatering aroma of fried dough when bitten or torn into. The only downside? They don't come cheap. Not at all.
Frosted Chocolate Cake Doughnut at Delicious Donuts
Second in popularity only to Voodoo, Delicious Donuts opens at 3 a.m. every day and typically sells out by 9 a.m., which quite frankly is surprising, because most of this shop's wares are soundly mediocre. That said, the chocolate-frosted chocolate cake doughnut is among the best we've eaten anywhere. Imagine a dense, moist, perfect chocolate birthday cake minus the dripping candles and overabundance of frosting and you're in the ballpark. Sprinkles optional.
Cinnamon-Sugar Doughnut at Moody's Donuts/Rocking Frog Café
After the health department forced the actual doughnut production from its original backyard shack into the adjacent Rocking Frog Café, Portlanders now have access to Moody's ultra-fresh, piping-hot wares seven days a week. Amen. Any variety will put a smile on your face, but the made-to-order cinnamon-sugar variety gets our vote. Hot from the fryer, the crisp shell emits an audible crunch as your teeth burrow into a melt-in-your-mouth interior.
Dark Fix at Acme Donuts
Situated on an unexceptional stretch of SE Powell, Acme Donuts can be missed easily by motorists rushing home after a hard day's work. Too bad, because it's clearly an up-and-comer in the Portland doughnut world. The best of the lot: the Dark Fix, a chocolate cake creation glazed in a rich, bitter dark chocolate and milk chocolate shavings. The cake itself is remarkably moist, with a buttery flavor and tenderness unlike any other doughnut in the city.
Acme Donuts: 2929 SE Powell Blvd., Portland, OR 97202 (map); (503) 233-6688
TIE! Frosted Cake and Apple Fritter at Coco Donuts
We tried to determine the superior doughnut here, but we proved incapable of such superfluous judgment. Both are magnificently tender sculptures of dough, with the simple cake doughnut showing just how important getting the little things right really is. Moist cake and an uncomplicated glaze with a nice homemade taste. The fritter is one of the softest we've ever eaten, in a nice departure from the overly solidified ones found at so many other shops. It doesn't overdo it on the cinnamon, and the bits of apple are crunchy and sweet. Don't even try to choose between these two, just buy 'em both.