đź“… Open Today: Crawl likely open on Saturdays
Explore Windsor’s vibrant nightlife with our food-centric pub crawl! Visit three fantastic venues — Toorak Hotel, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar — each offering delicious food, creative cocktails, and great vibes. Perfect for anyone looking to enjoy a fun night out, sample tasty bites, and sip on signature drinks in a friendly, lively setting. Whether you're a local or just visiting, this crawl is your ticket to a memorable evening!
Last updated: June 2025
Ready to ignite your night in Windsor? This bar crawl takes you on a spirited journey through some of the area’s most iconic and lively watering holes. Starting with the robust, food-forward atmosphere of Toorak Hotel, where hearty plates and classic drinks set a confident tone, you’ll then pivot to the playful and inventive cocktail scene at Better Days. Here, retro games and creative concoctions fuel the social buzz. Finally, the adventure crescendos at Blackwoods Wine & Cocktail Bar, where a refined yet animated crowd enjoys expertly crafted drinks in a welcoming setting. Each stop builds on the last, delivering an escalating energy that makes this crawl a must for anyone chasing excitement, great flavors, and memorable connections in Windsor’s nightlife.
The perfect launchpad for this crawl, Toorak Hotel combines hearty, satisfying food with classic pub energy, fueling the night with bold flavors and a lively dining scene that gets everyone ready for the evening ahead.
The next stop is a short, vibrant stroll to Chapel Street, letting the street's pulse build excitement as you head toward Better Days Cocktail Bar.
Bursting with playful energy, this spot injects fun and creativity into the crawl. Its inventive cocktails and retro gaming setup spark lively conversations and shared laughs, elevating the social vibe and sparking a youthful, adventurous spirit.
The next stop is just a few steps along Chapel Street, a bustling stretch alive with nightlife energy, guiding you seamlessly toward the elegant yet spirited Blackwoods Wine & Cocktail Bar.
Closing the crawl with style, Blackwoods offers a sophisticated yet inviting atmosphere, where expertly crafted cocktails and a vibrant crowd create the perfect setting for wrapping up the night with memorable toasts and animated conversations.
The next stop is the end of the crawl, leaving you perfectly placed to continue your Windsor night or head home with stories to tell.
This Windsor bar crawl delivers a night packed with flavor, fun, and social thrills — from hearty meals to creative cocktails and lively atmospheres. Whether you’re rallying friends or flying solo, this route keeps the energy flowing and the good times rolling. Ready to explore Windsor’s nightlife like never before? Grab your crew, hit these hotspots, and make tonight an adventure to remember.
Crawl Map