Washington DC Let’s face it -- 14th Street is a little intimidating, because something new opens every time a politician gets in trouble. Since you’re struggling to prioritize, here’s our take on a standout evening from start to finish. This is one of the tightest crawls you’ve ever seen though, so don’t count this as workout. Just relax and celebrate that it’s the freakin' weekend.

Masa 14

Happy Hour: Masa 14
1610 14th Street
Cheers to any joint that has happy hour seven days a week, especially when $4 margaritas are involved. Though you can get in on happy hour in the bar and lounge, why wouldn’t you head up to their sweet roof deck? Beer, wine, and a few more cocktails are also $4, plus small plates are on offer -- but don’t go crazy, because dinner’s next. Continue Reading

Michael Schlow

Dinner: Tico
1926 14th Street
Don’t lie DC, you live for what’s new. So grab a table at Tico because the doors just swung open. Feast on seven types of tacos and small plates like mac and cheese loaded with ingredients from Spain -- serrano ham and manchego cheese. If you can’t decide between the restaurant’s 45 dishes, give them a price point and they’ll just feed you. You’ll be drinking tequila -- they have 140 different selections.

Leo Schmid

After-Dinner Drinks: 2 Birds, 1 Stone
1800 14th Street
Actually, make that drink, singular. That’s because a typical tipple will cost you $14, but it’s worth it. After all, they’re one of the best new bars in America. The cocktail menu is always changing, which is exhausting considering the menu is hand-drawn comic book-style and involves crafting things like homemade carrot soda. Grab a sweet little nook and be sure to visit the racy bathroom.

Laura Hayes

Dessert: Red Light
1401 R Street
Your second stomach (which's reserved for dessert only) is grumbling. If only 14th Street had a place that just served sweets. Oh wait, there’s Red Light! Snag a patio table and order a set of the addictive Black & Tan Donuts stat. You’ll still be thinking about those pale ale beignets with stout chocolate filling tomorrow. Keep the buzz going with cocktails from the Wilder Brothers like a Sazerac or the Doubledown.

Black Jack

Keep the Party Going: Black Jack
1612 14th Street
Bocce games protected from the elements (especially oppressive humidity). A healthy dose of jostling around among hoards of young single people. A nice Summer Hofbrau Hefeweizen on draft. And creative cocktails like the Grilling Season, made with Balcome Brimstone whisky, Laphroaig, Aperol, and Dolin Blanc. These are the makings of a great spot to close the night. Attention first-timers: Black Jack is above Pearl Dive, look for the stairs.

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1. Masa 14 1825 14th St NW, Washington, DC 20009 (U Street)

The culinary lovechild of chefs Kaz Okochi (Kaz's Sushi Bistro) and Richard Sandoval (Zengo), Masa fuses the talents of both into a pleasing array of Latin/Asian small plates, in a handsome, open-kitchen 100-seater.

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2. Tico 1926 14th St NW, Washington, DC 20009 (U Street)

The bright and graffic graffiti murals are the first clues that your visit to Tico, an outpost of original Boston tapas bar, is going to be a colorful one. Inspired by Schlow's travels in Latin America, Spain, and Mexico, Tico offers bold small plates with Latin leanings, like roasted cauliflower with cotija cheese, black bass ceviche, and a velvety tres leches cake for dessert. There are multiple taco varieties too, but what keeps fans coming back for more are the addictive hibiscus margaritas.

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3. 2 Birds 1 Stone 1800 14th St NW, Washington, DC 20009 (Logan Circle)

Situated in Logan Circle, 2 Birds 1 Stone may be hidden beneath Doi Moi off bustling 14th Street, but it’s far from unknown in the DC cocktail world thanks to its expertly crafted concoctions. The chic, often-crowded bar is known for its original creations (check out the punch du jour) and its re-imagined classics, such as a tequila-infused dark & stormy. The stylish, subterranean space is surprisingly bright, sporting plush seating and exposed brick.

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4. Red Light 1401 R St, Washington, 20009 (Logan Circle)

The Red Light Bar is a tongue-in-cheek nod to the harrowing past of 14th Street NW and an homage to burlesque, though, thankfully, the cocktail and dessert bar’s décor is light on the red-light theme (apart from a silhouette of a woman in a corset in the mirror). The bar is concrete, and the room is dominated by shades of gray, suitable for the multitude of black-and-white images of 14th street that lines the walls. While Red Light offers appetizers and flatbreads like bacon-wrapped dates and pesto paninis, you’ll likely pay a visit for the dessert selection -- Snickers Pie, jumbo ice cream sandwiches, and the Sundae of the Month are simply too decadent to pass up.

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5. Pearl Dive Oyster Palace and Black Jack 1612 14th St NW, Washington DC, DC 20005 (Logan Circle)

Who says you can't play bocce while shooting oysters and sipping seasonal craft cocktails? Enjoy the Southern hospitality and the rustic, ancient mariner-inspired interior, while the chef shucks the best mollusks the East and West Coasts have to offer. They also have a solid happy hour with vodka martinis and a wine list with plenty of bottles that'll pair just right with your shelled snacks.