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Best Cookie/Cupcake: Two Fat Cats
Need to charm someone? Want to woo a prospective lover? Crave a shameless moment with a whoopie pie? Get thee to Two Fat Cats. Their cakes, cookies, and cupcakes are straight-up, drop-everything good. And their pies — bring one to a holiday party and you run the risk of showing up those in your family who spent the last 24 hours baking. We’ve loved descending into this sugary den of delights to get our fix for years; apparently we’re not alone.
47 India St, Portland | 207.347.5144 |

Best Dessert Place + Best Ice-Cream Parlor: Gelato Fiasco
This company might be changing the definition of the word “fiasco” the world over. Locals, tourists, and cruise-ship passengers alike flock to the Fore Street shop in Portland, where a gleaming display case shows off brightly colored tubs of handmade gelato and sorbetto in flavors you’ve never imagined in a frozen dessert (recent highlights include mint julep sorbetto for Kentucky Derby day and Corona and lime sorbetto for Cinco de Mayo). Beyond dairy-free and gluten-free options, the folks at Fiasco also offer the richest dark chocolate and brightest vanilla flavors in the city. With free samples, unlimited combinations, and cheerful service, your sweet tooth and your belly will thank you in equal measure.
425 Fore St, Portland | 207.699.4314 | 74 Maine St, Brunswick | 207.609.4262 |

Best Diner: Becky’s
Sometimes you just want breakfast, right? Becky’s fits the bill — when it’s not overflowing with other people who had the same idea, that is. No-nonsense, open super-early (or super-late, depending on whether you’re a fisherman or...22 years old), and known for serving straight-up diner classics with a begrudging smile, this tourist mecca on Hobson’s Wharf is also looked on quite affectionately by locals. The muffins have quite a good reputation, and the lobster omelette is an out-of-towner’s dream. We happen to think the pancakes are damn tasty.
390 Commercial St, Portland | 207.773.7070 |

Best Dive Bar: Ruski’s Tavern
Ruski’s is a Portland treasure, a true neighborhood bar, and the closest thing to Cheers this side of 9/11. Some bars try to appropriate “dive” status by serving too-stiff drinks, shitty fries, and failing to wash their bathrooms. Ruski’s comes at it the natural way, by creating an atmosphere where you can be your raw, unfiltered self. Sports are present but not the focus, food is deceptively good, and the drinks are...well, yeah, they’re still pretty stiff. Some of the best moments in Portland can be had at Ruski’s, whether spending a snowed-in morning eating breakfast or catching an impromptu Darien Brahms set. We love it here, and it’s not going away anytime soon.
212 Danforth St, Portland | 207.774.7604

Best Drink Deal: $2 Happy Hour at the Front Room
Imagine a world where “Happy Hour” wasn’t the slice of time between work and home...wait, that’s a depressing start. But isn’t that what this in-between time is for? To let your mind run wild, to think the thoughts you push aside for the rest of the ho-hum day? Truth is, we’ve availed ourselves of several a $2 glass of wine during Happy Hour from 4-6 pm at the Front Room, Munjoy Hill’s neighborhood eatery. And something about the setting — maybe the coziness of the room, or the view of people walking home from their jobs, or the knowledge that your own couch is just around the corner — makes this the perfectly affordable two-hour span in which to contemplate the big questions be they comfortable or not.
73 Congress St, Portland | 207.773.3366 |

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