đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant cocktail scene with our exclusive bar crawl! Explore three quirky neighbourhood hangouts — Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar — each offering unique vibes, delicious drinks, and lively DJ parties on weekends. Perfect for a fun night out with friends, this crawl combines cozy snugs, creative cocktails, and great music. Book your spot and make your Windsor night unforgettable!
Last updated: July 2025
Windsor’s Chapel Street is your playground for an electrifying cocktail adventure that pulses with energy and social buzz. Start at Three Monkeys, where quirky charm meets upbeat beats, setting the perfect tone for an exciting night ahead. From there, pivot to the playful world of Better Days Cocktail Bar, where classic games and inventive drinks spark friendly competition and laughter. As the night peaks, Blackwoods Wine & Cocktail Bar invites you to indulge in refined cocktails and a vibrant crowd, wrapping up your crawl with a spirited sense of connection and celebration. This crawl isn’t just a route—it’s a curated journey through Windsor’s lively cocktail culture, designed for those ready to toast, mingle, and make memories.
Launching your crawl at Three Monkeys means diving headfirst into a spirited atmosphere where quirky interiors and weekend DJ beats ignite the night. It’s the perfect energizer, mixing expertly crafted cocktails with an infectious vibe that sparks conversation and dance alike.
The next stop is a quick, vibrant stroll down Chapel Street, keeping the momentum alive while transitioning to a more playful, social setting.
Better Days brings a lively twist with its mix of lounge comfort and interactive fun. Here, classic video and board games pair seamlessly with inventive cocktails, making it the ideal spot to deepen connections and amplify the night’s energy through shared laughs and spirited competition.
The next stop is a short, energizing walk further along Chapel Street, shifting the vibe into a chic yet inviting space perfect for rounding out the evening.
Concluding the crawl at Blackwoods Wine & Cocktail Bar brings a sophisticated crescendo to your night. With a finely curated wine list and masterful cocktails served in a lively yet polished setting, it’s where vibrant conversations flow and the night’s adventurous spirit finds its perfect finish.
The next stop is the end of this curated crawl, leaving you perfectly poised to continue your Windsor night or savor the memorable finale.
This Windsor cocktail bar crawl delivers a dynamic night filled with rhythm, playfulness, and elegance—each stop a fresh chapter in your evening’s story. Whether you’re a cocktail connoisseur or a social adventurer, this journey along Chapel Street promises vibrant vibes and memories to toast for nights to come. Ready to raise your glass and dive in? The night is calling.
Crawl Map