đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant cocktail scene with our curated crawl through five fantastic venues. Sip on rum and creative cocktails in cozy, ship-themed bars like Holy Grail, enjoy the plant-filled lounge at Jungle Boy, or unwind at Better Days with tiki mugs and trendy vibes. From plush couches at Three Monkeys to lively DJ parties on weekends at Blackwoods, this crawl offers a perfect mix of quirky neighborhoods, great drinks, and good times. Grab your friends and let's make it a night to remember!
Last updated: July 2025
Get ready to own the night with the Windsor Cocktail Bar Crawl, a carefully curated journey through Chapel Street’s most vibrant cocktail destinations. This crawl kicks off with Three Monkeys, where quirky charm and weekend DJ energy set an inviting tone. As the night flows, Better Days injects playful competition and inventive mixes, sparking laughter and connection. Blackwoods steps up the sophistication with masterful cocktails and a welcoming buzz, perfect for gathering your crew. The adventure continues aboard the ship-inspired Holy Grail, where smooth rums and cozy corners invite you to unwind without losing the buzz. Finally, Jungle Boy’s lush tropical setting and daring tiki concoctions provide a memorable crescendo, leaving you energized and thrilled. Each stop is a pulse in the beating heart of Windsor nightlife—expect energy shifts, playful contrasts, and nonstop social excitement from start to finish.
Launching your crawl with Three Monkeys sets a lively yet intimate tone. Its quirky, snug setting and weekend DJ sessions create an energetic atmosphere that invites both conversation and celebration, priming you for an unforgettable night ahead.
The next stop is a brief, invigorating stroll down Chapel Street to Better Days, keeping the momentum high and anticipation building.
Better Days ramps up the fun with its playful mix of board games, video classics, and inventive cocktails, transforming the night into a social playground where laughter and friendly competition fuel the vibe.
The next stop is a short, energizing walk along Chapel Street to Blackwoods, allowing the excitement to evolve naturally.
Blackwoods brings a tasteful shift with expertly crafted cocktails and curated wines in a space that balances lively social energy with elegant comfort—a perfect pitstop to savor quality and camaraderie.
The next stop is a quick, inviting walk to Holy Grail, keeping the crawl’s vibrant energy flowing seamlessly.
At Holy Grail, the crawl takes on a cozy yet spirited atmosphere with its ship-themed décor and rich rum selection, inviting group revelry without losing the intimate connection between friends.
The next stop is a lively stroll down Chapel Street to Jungle Boy, prepping you for the crawl’s tropical finale.
Jungle Boy closes the night with a burst of tropical energy, where lush plants and exotic tiki cocktails spark a festive, adventurous mood, ensuring your Windsor night ends on a high and memorable note.
The crawl concludes here, leaving you perfectly positioned to continue your night or savor the afterglow.
The Windsor Cocktail Bar Crawl isn’t just a night out—it’s an expedition through Chapel Street’s most thrilling cocktail scenes. From quirky beginnings to tropical finales, this adventure invites you to mix, mingle, and make memories at every turn. Ready to take on the night? Gather your crew, lace up your walking shoes, and let Windsor’s cocktail treasures ignite your next unforgettable social adventure.
Crawl Map