A date plan
Hangout · Williamsburg · Casual · $$
A laid-back Williamsburg evening that moves from a cozy Mexican spot with killer agave cocktails to a vine-covered Italian garden bar, then caps the night with vintage pinball and cold beers.
Williamsburg · $$$ · Mexican restaurant · Delivery Restaurant
De Mole is the kind of neighborhood gem that doesn't need to try hard — the food does the talking. Order the signature mole (obviously) and let whoever's most indecisive at the table just point at something with an agave spirit in it. The space is relaxed and unfussy, exactly what you want before a full night out.
~8 min walk (0.4 mi). Walking from de Mole to Aurora, you'll pass through the heart of South Williamsburg — keep an eye out for the murals along Grand St, there's always something new going up.
Williamsburg · $$$ · Bar · Italian restaurant
Aurora has been a Williamsburg institution since 2003, and that ivy-covered back garden is still one of the best places in the neighborhood to linger over a glass of wine with a group. Post-dinner, grab a spot outside and work through their 150-bottle wine list — or just ask the server what's good by the glass. Either way, you're not rushing out of here.
~9 min walk (0.5 mi). From Aurora to Jackbar, you're heading deeper into Williamsburg's residential grid — a nice moment to stretch your legs and let the wine settle before the pinball wars begin. Note: Jackbar is on Havemeyer St, which sits a few blocks east of the Bedford Ave core — still very much Williamsburg, just a touch off the main drag.
Williamsburg · $ · Bar
Jackbar is the perfect low-key closer — a room packed with vintage pinball machines, no attitude, and cheap drinks. It's got outdoor tables if the group needs air, and the competitive energy of a pinball tournament between friends is exactly the kind of thing that turns a good night into a great story. Quarters up.