đź“… Open Today: Crawl likely open on Sundays
Embark on a delicious journey through Woollahra with our Food-Centric Pub Crawl! Experience the best of Italian cuisine at I Maccheroni, indulge in gourmet dishes at Paddo Inn, savor European comfort food at Imperial Hotel Paddington, and enjoy craft beer at Winghaus Entertainment Quarter. Get ready for a night of culinary delights and great drinks in a vibrant and welcoming atmosphere!
Last updated: May 2025
Dive headfirst into Woollahra’s dynamic pub scene with this electrifying 4-stop crawl designed for those who crave a night packed with flavor, style, and spirited social energy. Begin your journey amid the rich aromas and handcrafted pasta of an intimate Italian osteria, setting a sumptuous foundation. Then, step into Paddo Inn’s polished setting where expertly mixed cocktails and worldly fare elevate the mood, blending sophistication with buzzworthy conviviality. As the evening unfolds, the Imperial Hotel welcomes you with its rustic-chic warmth and classic pub charm, offering a textured contrast that fuels lively conversation and connection. Finally, cap off your adventure at Winghaus in the Entertainment Quarter, where bold craft brews meet hearty European comfort food in an upbeat, communal atmosphere that keeps the good times rolling. This crawl isn’t just a night out—it’s a curated social adventure through Woollahra’s spirited pub tapestry.
Start your crawl immersed in authentic Italian passion where fresh pasta spun daily and a curated wine list ignite your night with warmth and vibrant flavor, setting an energetic tone for the adventure ahead.
The next stop is a brisk 10-minute walk along Jersey and Oxford Streets, perfect for digesting those rich flavors while gearing up for a stylish shift in atmosphere.
Paddo Inn amps up the energy with its elegant fusion of global cuisine and cocktail craftsmanship, offering a spacious, chic backdrop that invites lively chats and spirited toasts as the night unfolds.
The next stop is a quick 5-minute stroll down vibrant Oxford Street, transitioning smoothly from polished sophistication to rustic charm.
Step into the Imperial Hotel’s rustic-chic embrace where leather armchairs, fireplaces, and hearty fare create a dynamic contrast to earlier stops, fueling conversation and camaraderie with its timeless pub spirit.
The next stop is a lively 15-minute walk through Paddington’s streets towards Moore Park’s Entertainment Quarter, building anticipation for a bold craft beer finale.
Conclude your night at Winghaus, where craft ales flow freely and European comfort foods like schnitzels fuel an upbeat, communal vibe—perfect for celebrating the night’s adventures with new friends.
The crawl ends here, leaving you perfectly positioned to explore more of the Entertainment Quarter or head home exhilarated from a night well spent.
Celebrate Woollahra’s vibrant pub culture with this carefully curated crawl that blends rich flavors, stylish settings, and lively atmospheres into one unforgettable night. Whether you’re raising your glass over Italian classics, toasting with artful cocktails, sinking into rustic charm, or sharing craft brews among new friends, this adventure keeps the energy high and the good times flowing. Lace up your walking shoes, gather your crew, and get ready to explore Woollahra’s spirited nightlife—each stop promising fresh excitement and social sparks. Cheers to your next great night out!
Crawl Map