đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's top cocktail and wine bars on this lively pub crawl! Visit 3 fantastic venues—Ruelle Wine Bar, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering unique drinks, great food, and vibrant atmospheres. Perfect for anyone looking to enjoy a relaxed yet energetic night out with friends, exploring the city's best bars and hidden gems. Cheers to good times and great drinks in Windsor!
Last updated: July 2025
Fuel your night with a cocktail bar crawl that pulses with energy and social adventure in Windsor’s iconic Chapel Street precinct. Kick off your evening at Ruelle Wine Bar, where an impressive wine collection and artisanal bites set the stage for an engaging start. From there, dive into a spirited atmosphere at Better Days Cocktail Bar, where retro games meet inventive drinks — sparking laughter and friendly competition. Finish strong at Blackwoods Wine & Cocktail Bar, a hotspot blending expert mixology with a buzzing crowd, perfect for toasting to a night well spent. This crawl crafts a dynamic flow of flavors and vibes, ensuring every stop elevates your social escapade.
Ruelle Wine Bar launches the crawl with its refined wine selections and thoughtfully paired bites, offering an elegant yet lively entry point to set a spirited tone.
The next stop is a short, vibrant stroll down Chapel Street, where the energy shifts from sophisticated wine tasting to playful cocktail creations.
Better Days injects the night with its infectious energy — think inventive cocktails paired with nostalgic games, creating a social playground that sparks fun and connection.
The next stop is just a quick walk along the lively Chapel Street strip, guiding you towards expertly crafted cocktails in a buzzing environment.
Blackwoods delivers a high-energy finale with its polished cocktail craft and welcoming vibe, the perfect backdrop for vibrant conversations and celebratory toasts.
The crawl concludes here, right in the heart of Chapel Street’s nightlife, with no further walking required.
Wrap up your Windsor cocktail adventure at Blackwoods, savoring the last sips amid a lively crowd. Ready to conquer the night? This crawl promises a seamless journey through engaging flavors, vivid atmospheres, and unforgettable social moments. Gather your crew, charge your spirits, and let Windsor’s cocktail scene sweep you into an energetic celebration of taste and camaraderie.
Crawl Map