đź“… Open Today: Crawl likely open on Sundays
Get ready for a night of fun in Woolloomooloo with our Rooftop Pub Crawl Extravaganza! Visit 4 venues including The Old Fitzroy Hotel, Sweethearts Rooftop, Darlo Bar, and East Village Hotel Sydney. Enjoy a mix of intimate 2-storey bars, eclectic 1960s-style rooms, and a bustling pub with rooftop views. Food-centric options available at every stop. Let's make it a night to remember!
Last updated: May 2025
Kick off your night in Woolloomooloo with a bar crawl that punches up the energy and takes you on a rooftop adventure filled with style, flavor, and unforgettable city scenes. Starting at a beloved historic pub with its intimate theatre and hearty fare, the journey escalates to a Mexican-inspired rooftop with cocktails as bold as the skyline views. From there, dive into a vintage 1960s vibe where craft drinks and eclectic design spark lively conversation. Finally, ascend to a lush rooftop terrace pulsing with DJ beats and panoramic city lights — a perfect crescendo to an exhilarating night out. This crawl is crafted for those craving social buzz, spirited drinks, and a memorable night above the city streets.
Your launchpad for the night, The Old Fitzroy Hotel radiates historic charm and buzzing energy with its exposed-brick walls and intimate theatre vibe. It sets a spirited tone, fueling the group with hearty bites and a dynamic crowd before the rooftop escapades begin.
The next stop is a brisk, lively stroll to Sweethearts Rooftop, offering a refreshing change of pace and atmosphere just a few minutes away.
Up next, Sweethearts Rooftop lifts the vibe with dazzling skyline views and vibrant Mexican-inspired cocktails and cuisine. Its open-air terrace invites you to soak in the city’s pulse while savoring bold flavors, perfect for elevating the night’s momentum.
The next stop is a short and energetic walk into Darlinghurst, transitioning the scene towards retro-chic vibes at Darlo Bar.
Darlo Bar injects the evening with 1960s flair and a buzzing rooftop cocktail scene. Its eclectic décor and craft drinks create a playful, social atmosphere where the night’s energy peaks with vintage cool and creative libations.
The next stop is a quick walk that leads you to the final rooftop destination, setting the stage for a grand finale with sweeping cityscape views.
Closing out the crawl, East Village Hotel’s rooftop terrace dazzles with lush greenery, twinkling lights, and vibrant DJ beats. This multi-level hotspot amps up the party atmosphere, offering a perfect blend of lively crowd energy and breathtaking city vistas to celebrate the night’s adventure.
The next stop is the crawl’s finale, so here you can settle in and revel in the rooftop buzz without the need to move on.
This Woolloomooloo rooftop bar crawl masterfully blends historic charm, bold international flavors, retro flair, and vibrant rooftop scenes into one electrifying night. Whether you’re gathering with friends or diving into Sydney’s energetic nightlife solo, each stop keeps the excitement soaring and the social vibes alive. Ready to claim your spot above the city lights? Grab your crew, pace yourself, and let this rooftop adventure become your new favourite night out.
Crawl Map