A date plan
Date · Prospect Heights
A Vanderbilt Ave wine bar kick-off flows into an intimate dinner at a beloved neighborhood gem, then caps the night with pastries and cocktails at the all-day café from one of Brooklyn's best culinary teams.
Prospect Heights · $$ · Wine bar
Wallace is the kind of wine bar that makes you want to linger — snug, candlelit, and stocked with a rotating list of natural and low-intervention pours. Pull up a seat at the bar, let whoever's pouring talk you through something orange or funky, and let the night find its footing. It's the perfect low-key opener that still feels like a real occasion.
~5 min walk (0.3 mi). From Wallace, stroll south down Vanderbilt Ave — the brownstone-lined blocks are at their most atmospheric after dark. Keep an eye out for the little garden stoops and fairy-lit windows as you wind toward Dean St.
Prospect Heights · $$$ · American restaurant · Bakery
Leland Eating and Drinking House is exactly what its name promises — unhurried, intimate, and deeply thoughtful. The menu leans into beautifully sourced ingredients with a Mediterranean tilt: expect elegant small plates, a smart wine list that complements rather than competes, and a room that feels like a well-kept secret even on a busy night. This is the kind of dinner where the conversation flows as easily as the wine.
~10 min walk (0.5 mi). Leland to Cafe Mado is a quick hop over to Washington Ave — a reminder of just how walkable and neighborhood-y Prospect Heights really is. Note that Cafe Mado sits slightly toward the Crown Heights border, but it's firmly in the spirit (and stomping grounds) of the Heights crowd.
Prospect Heights · $$$ · Restaurant
Cafe Mado — from the lauded team behind Oxalis — is a gorgeous way to close the evening: think laminated pastries, house-made gelato, and cocktails in a space that's equal parts chic and welcoming. Share a dessert plate and linger over a digestif; there's no rush here. It's the rare spot where you genuinely don't want to leave.