đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant cocktail scene with our fun-filled crawl through 3 unique venues: Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. This quirky neighbourhood hangout offers snug spots, creative drinks, and lively DJ parties on weekends. Perfect for those looking to explore Windsor’s best bars with friends, enjoy great vibes, and sip on expertly crafted cocktails in a friendly, relaxed atmosphere. Let’s make your night unforgettable!
Last updated: July 2025
Dive headfirst into Windsor’s cocktail playground with this dynamic bar crawl designed for thrill-seekers and cocktail aficionados alike. Begin your night at Three Monkeys, where quirky charm and weekend DJ beats set an electrifying tone. The energy then shifts to Better Days Cocktail Bar, blending nostalgia with inventive cocktails and a lively social scene fueled by classic video games and board games. Finally, wind your way to Blackwoods Wine & Cocktail Bar, where sophisticated mixology meets a welcoming atmosphere—perfect for toasting new friendships and unforgettable memories. This curated journey balances upbeat beats, playful spirit, and refined flavors, crafting an adventurous night that keeps the momentum flowing until the last sip.
As the energetic launchpad of your crawl, Three Monkeys injects vibrant vibes with its eclectic décor, expertly crafted cocktails, and weekend DJ sets that ignite the night’s pulse from the first pour.
The next stop is a short stroll down Chapel Street, keeping the buzz alive as you head toward a more playful and interactive scene.
Better Days amps up the fun factor with its nostalgic gaming corner and inventive cocktails, offering a lively social playground that invites laughter, friendly competition, and shared moments among friends.
The next stop is just a brisk walk further along Chapel Street, transitioning you smoothly into a more sophisticated yet equally vibrant atmosphere.
As the grand finale, Blackwoods elevates the experience with refined mixology and a warm, inviting ambiance—perfect for savoring crafted cocktails while soaking up Windsor’s night-time charm.
The next stop concludes the crawl here, allowing you to settle in and celebrate the night’s spirited journey.
Ready to turn up the energy and discover Windsor’s cocktail treasures? This crawl promises an exhilarating blend of beats, games, and top-tier drinks that will have you and your crew buzzing all night long. Whether you come for the crafted cocktails, the lively vibes, or the social sparks, each stop delivers a unique slice of Windsor’s vibrant nightlife. Lace up your walking shoes, bring your best crew, and let this cocktail adventure write the story of your next unforgettable night out.
Crawl Map