đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant cocktail scene with our fun-filled crawl through three top venues: Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Perfect for those who love snug, quirky neighbourhood hangouts with great drinks and lively DJ parties on weekends. Whether you're after creative cocktails or relaxing wines, this crawl offers a fantastic mix of venues to make your night memorable. Grab your friends and get ready for an unforgettable Windsor experience!
Last updated: July 2025
Windsor’s Chapel Street pulses with some of the city’s most dynamic cocktail bars, and this crawl is your ticket to an evening packed with flavor, flair, and fantastic company. Begin your adventure at Three Monkeys, where infectious energy from weekend DJs and expertly crafted cocktails set the tone for an exciting night. Next, shift gears at Better Days, a vibrant spot where nostalgia meets inventive mixology — think board games, video classics, and a lively atmosphere that keeps the good times rolling. Finally, round off your journey at Blackwoods Wine & Cocktail Bar, a sophisticated yet approachable venue that effortlessly balances elegant cocktails with a warm, inviting crowd. Together, these stops create a seamless progression of energy and vibe, transforming your night into a spirited social escapade.
Kick off the crawl at Three Monkeys, where quirky charm meets high-energy cocktail craftsmanship and weekend DJ sessions, igniting the night with vibrant rhythms and welcoming buzz.
The next stop is a short, lively stroll down Chapel Street, keeping the night’s momentum as you head toward Better Days.
Better Days amps up the fun with its playful mix of inventive cocktails, classic video games, and a spirited crowd, delivering a fresh burst of energy and social playfulness.
The next stop is just a brisk walk further along Chapel Street, allowing you to savor the vibrant neighborhood vibe en route to Blackwoods.
Conclude the crawl at Blackwoods, where elegant cocktails and a friendly atmosphere provide the perfect setting to wind down while keeping the night’s lively spirit alive.
The crawl ends here, so you’re perfectly placed to continue exploring Windsor’s nightlife or call it a night with a memorable final sip.
From infectious beats and quirky cocktails to nostalgic games and elegant finishes, this Windsor cocktail crawl serves up an exhilarating night out that’s as social as it is spirited. Gather your crew, pace yourself, and dive into the vibrant pulse of Chapel Street’s best bars. Ready to make memories and raise glasses? Your Windsor adventure awaits.
Crawl Map