đź“… Open Today: Crawl likely not fully open on Sundays
Embark on a wine bar adventure in Redfern, exploring 7 unique venues. Start at Bar Cleveland for a cozy atmosphere, then head to Mille Vini Wine Bar & Restaurant for rustic European dishes. Continue to The Winery for a classy upscale experience and BART Jr. for craft beer delights. Don't miss out on Bistro St Jacques for French bistro staples and Berkelouw Café 1812 for high tea in a licensed bookshop setting. Wrap up your night at Vintage Cellars Darlinghurst for a selection of fine wines. Cheers to a memorable crawl!
Last updated: May 2025
Berkelouw Books Level One, 19 Oxford Street, Paddington
~705m walk to next stop
Kick off your night in Redfern with an adventurous wine bar crawl that pulses with energy, character, and bold flavors. This carefully curated 7-stop journey takes you from a lively heritage-listed pub through rustic Italian-inspired tasting rooms to bohemian laneway gems. Along the way, you’ll dive into inventive shared plates, organic wine selections, and buzzing atmospheres that spark conversation and connection. Each stop elevates the vibe—starting with warm, historic comfort and building through sophisticated, stylish settings to a spirited finale, ensuring every sip and step amps up the excitement. This is more than a crawl; it’s a social exploration where wine lovers and night owls unite for a dynamic, taste-driven adventure in one of Sydney’s most vibrant neighborhoods.
Launch the night at Bar Cleveland, where heritage-listed charm meets bustling energy. Its multiple bars and lively cocktail scene set a spirited tone, inviting you to mingle amid warm lighting and lush greenery before diving deeper into Redfern’s wine scene.
The next stop is a short, energizing stroll that shifts the vibe from classic pub buzz to rustic European elegance.
Step into Mille Vini’s rustic sophistication, where handcrafted pastas, tasting plates, and curated wines bring a cozy yet vibrant European flair. This stop deepens the culinary journey with warm ambiance and a touch of jazz-infused excitement.
The next stop is a brief, lively walk that ushers you into a stylish bohemian laneway setting, perfect for savoring modern Australian flavors.
Discover The Winery’s chic bohemian vibe, where abundant wine options and fresh modern Australian dishes pair perfectly with lush outdoor seating. This stop elevates the crawl’s sophistication while keeping it fresh and social.
The next stop is a quick walk back toward Redfern’s vibrant heart, shifting from upscale laneway cool to a spirited local favorite with a craft edge.
BART Jr. brings a burst of vibrant energy with seasonal pub food, craft beers, and a standout wine list. Its lively atmosphere and shared plates make it a social hotspot, fueling connection and good times mid-crawl.
The next stop is a brisk stroll just down the street, shifting gears toward classic French bistro comfort with a modern twist.
Immerse in authentic French flavors and organic wines at Bistro St Jacques, where cozy old-school charm meets attentive service. This stop offers a rich, food-focused pause that complements the crawl’s rising energy with timeless sophistication.
The next stop involves a friendly walk extending into Paddington, transitioning from intimate bistro vibes to a bright, literary-inspired café scene.
Berkelouw Café 1812 invites you to unwind among bookshelves with quality wines and share plates in an airy, retro-chic bookshop setting. This spot adds a unique cultural twist to the crawl, blending conviviality with a touch of literary charm.
The next stop is a lively walk along Oxford Street into Darlinghurst, gearing up for a neighborhood wine and spirits finale.
Cap off the adventure at Vintage Cellars Darlinghurst, a no-fuss local hub offering a wide array of wines and spirits. This spot provides a practical yet welcoming conclusion to your crawl, perfect for picking up a favorite bottle or savoring the last tastes of the night.
The crawl concludes here, with Vintage Cellars providing an easy exit or a last spirited stop to toast your night.
This 7-stop wine bar crawl through Redfern and its vibrant neighbors is your ticket to an unforgettable night of discovery, flavor, and social connection. From historic pubs to bohemian hideaways and cultural cafés, each venue amps up the excitement and invites you to savor every moment. Whether you’re raising a glass with friends or immersing yourself in Sydney’s eclectic wine scene, this crawl promises adventure in every sip and step. Ready to explore? Grab your crew, map your route, and dive into the dynamic pulse of Redfern’s wine bars tonight.
Crawl Map