December 21st is the longest night of the year (that’s the Winter solstice to all you non-Pagans), but it’s also going to be the Best Night of Your Life, a Thrillist-created holiday that you'll spend enjoying the best nightlife the city has to offer, thanks to our awesome recommendations, which obviously include Portland's best late-night eats.
Departure Downtown Named our favorite outdoor patio this past summer, don’t think for a second this place is any less cool because it’s like, cold and rainy. Departure's bold Asian flavors (BBQ short-rib buns, sweet chili-glazed wings, etc.) are the perfect respite from the weather -- which you can totally see heading your way from the 15th floor of the Nines hotel smack dab in downtown.
Nostrana Buckman This quaint Italian spot is the perfect place to bring your sweetheart and share a bottle of wine, smelling the wood-fired everything and sighing into each other’s eyes over candlelight... but since this is the Best Night of YOUR Life, you can also saddle up to the bar and dive into a few of the city’s best Negronis before ordering one or four of the city’s best Neapolitan pizzas.
Cibo Division / Clinton You’ll find Cibo on that southeastern stretch of Portland known as Division - the quiet, unassuming little spot might be easy to miss, and the leather-lined, wood-fired restaurant might seem ordinary, but the pizzas are... err, the-opposite-of-ordinary, and (oh, yeah) they only cost $5!
Savoy Tavern Division / Clinton This dark, candlelit comfort foodery is slinging a bevy of Midwest-style eats ranging from Wisconsin's best invention (fried cheese curds), to braised pork cheeks, to roasted rabbit hindquarters, which is actually the thing on the menu that's best for your middle.
Driftwood Room Goose Hollow A recently refurbished dark wood and leather-heavy bar located in the old school Hotel Deluxe, this stylish drinkery boasts sweet eats from neighboring restaurant Gracie’s, and a little bit of Hollywood glamor, which is why it doesn't just serve Negronis and Boulevardiers, it serves them w/ rum-soaked pieces of fruit they set on fire.
Doug Fir Lounge East Burnside This swank lounge and music venue attached to one of our hippest hotels is decorated almost entirely with... surprise!... wood, comes with a covered patio complete with fire pit, and a line up of sweet cocktails, including a tequila/ New Deal Ginger Liqueur/ Squirt combo called the Big Deal, though if you're not into any of that, you can always just make like a tree (though not a Douglas Fir since it isn't deciduous) and leaf.