With three bars, a Top Chef alum in the kitchen, and a cocktail program built around Miami’s sound, Upside is the latest signal that Wynwood’s nightlife has outgrown the mural.

Wynwood has always understood spectacle. The neighborhood built its reputation on the graffiti-lined walls of Wynwood Walls, on galleries that spill their openings onto the sidewalk, on a creative economy that treats the street itself as a canvas. What’s changed, in recent years, is the hour. Where Wynwood once emptied out after the last gallery closed its doors, the district’s bar rotation has increasingly bent toward something more ambitious: music-driven cocktail concepts, DJ-led rooms, spaces built to carry the neighborhood’s daytime energy straight through to last call.

Upside is the newest, and among the most fully realized, entries in that evolution. Now open at 59 NW 28th Street, the 8,500-square-foot venue spans two floors and a covered outdoor space, anchored by three distinct bars, a kitchen led by Top Chef Season 16 alum Pablo Lamon, and a cocktail program conceived in direct conversation with Miami’s music and art scenes.

A Room Built to Turn Over the Day

Upside’s architecture is designed around transition. The ground floor centers on a wrap-around bar, fronted by screens built for game-day watch parties and live sport — an unmistakably daytime proposition. But the room is engineered to shift: the outdoor bar extends the experience into open air, where lounge seating and dynamic lighting gradually pull the space into late-night territory as the sun goes down. Upstairs, a second bar and dining tables overlook the double-height main floor below, giving the upper level a kind of balcony-seat vantage point on the room’s own transformation.

It’s a layout that solves a problem many Wynwood venues have struggled with: how to be a credible afternoon destination and a credible midnight one without feeling like two different businesses stitched together. Upside’s answer is architectural — build the flexibility into the bones of the room, then let lighting and programming do the rest.

Courtesy of Upside Wynwood

Cocktails With a Point of View

The bar program balances signature invention against confident riffs on the classics, with seasonal rotation built in from the start. She’s Salty reworks the margarita as a low-sugar pour — Don Julio Blanco, Grand Marnier, pamplemousse liqueur, and monkfruit, finished with a salt foam. Trouble in Paradise leans sweeter, built on Grey Goose Vodka, dry vermouth, peach liqueur, and strawberry sherry syrup, garnished with a gummy bear that doubles as a wink at the room’s playfulness. Main Character Energy takes a mezcal-forward turn, blending 21 Seeds Orange and Union Mezcal with lime, agave, blueberry water, and crème de banane.

In the kitchen, Executive Chef Pablo Lamon has built a shareable menu calibrated for a bar-first crowd rather than a traditional dinner service — Braised Short Rib and Manchego Croquettes, Red Jalapeño Mac & Cheese Arancini, a Whipped Ricotta “Cream Cloud” toast, alongside more ambitious plates like Smoked Wagyu Sirloin Bites, Lobster Nuggets, and a Truffle Grilled Cheese Sandwich. The menu scales for groups by design, with tiered platters — Party for 4, Party for 6, and a caviar-topped We Fancy tier — built for the watch-party crowd Upside is clearly courting.

Courtesy of Upside Wynwood

Music as the Organizing Principle

What separates Upside from a well-executed cocktail bar is the degree to which music sits at the center of its identity rather than as ambience. The venue runs an evolving calendar of curated sets, DJ appearances, and late-night performances, with surprise sets and dedicated listening sessions built into the program. That cultural layer extends outward: cocktail collaborations with spirit brands, art and fashion pop-ups, and venue activations timed to Wynwood Art Walk and the FIFA World Cup’s Miami footprint.

It’s a strategy that tracks with where Wynwood’s hospitality scene is headed more broadly. Rather than standalone bars or restaurants, operators throughout the neighborhood are increasingly building flexible, experiential venues — spaces that braid nightlife, dining, music, and branded programming into a single, continuous offering that can move with the neighborhood’s cultural calendar instead of sitting outside it.

Courtesy of Upside Wynwood

A Neighborhood That Keeps Rewriting Its Own Night

Wynwood’s evolution from abandoned warehouse district to open-air gallery is well told at this point. What’s less discussed is the second transformation now underway — from an arts district with a few beloved dive bars into a genuine nightlife ecosystem, one where craft cocktail programs and chef-driven kitchens are as central to the neighborhood’s identity as its murals ever were.

Upside arrives squarely in that current, and lands as one of the strongest new additions to Wynwood’s rotation: a venue built not for a single moment in the evening, but for the full arc of a Miami night — from an afternoon watch party, through golden hour, into whatever the DJ booth decides comes next.

Upside is located at 59 NW 28th Street in Wynwood, Miami.