đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant cocktail scene with our fun-filled crawl through three unique venues: Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. This neighbourhood hangout offers a snug, quirky vibe perfect for drinks, dancing, and good times. Whether you're into creative cocktails or lively DJ parties on weekends, this crawl is your ticket to an unforgettable night out in Windsor’s coolest spots.
Last updated: July 2025
Kick off an unforgettable night in Windsor with a cocktail bar crawl that pulses with energy, creativity, and social adventure. This curated journey along Chapel Street invites you to explore three standout bars, each delivering a distinct vibe that elevates the night as it unfolds. Begin at Three Monkeys, where quirky charm meets lively DJ sets, setting a spirited tone. Then, tap into playful competition and inventive mixology at Better Days, a vibrant hub for friends and fun. Finally, wind down with sophistication and welcoming warmth at Blackwoods Wine & Cocktail Bar—an elegant yet approachable spot perfect for toasting new memories. This crawl isn’t just about drinks—it’s about the dynamic flow of atmospheres and the stories that come to life between sips.
Launching the crawl, Three Monkeys sets a high-energy tone with its quirky, intimate atmosphere and weekend DJ sessions that ignite the night’s excitement from the first cocktail.
The next stop is just a short stroll down Chapel Street, keeping the momentum alive with easy access to the next lively spot.
Better Days amps up the adventure with its playful mix of board games, video games, and inventive cocktails, offering a vibrant yet social playground to connect and compete.
The next stop is a quick and inviting walk along Chapel Street, transitioning smoothly toward a more refined cocktail experience.
Closing the crawl, Blackwoods delivers a sophisticated yet welcoming atmosphere with expertly crafted cocktails and a curated wine list, perfect for savoring the night’s last memorable moments.
The crawl culminates here, so no walking needed—just settle in and enjoy the final stop’s charming ambiance.
Embrace the pulse of Windsor’s cocktail culture on this dynamic crawl that promises excitement, connection, and expertly crafted drinks at every turn. Whether you’re a local or visiting, this curated route along Chapel Street invites you to taste, play, and toast your way through an evening packed with spirited vibes and unforgettable moments. Gather your crew and let the adventure begin—Windsor’s cocktail scene is ready to surprise and delight.
Crawl Map