đź“… Open Today: Crawl likely open on Fridays
Explore Windsor's vibrant cocktail scene with this fun-filled crawl through three quirky venues: Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Whether you're after a snug spot for craft cocktails or lively DJ nights on weekends, this crawl has it all. Perfect for those who love unique neighbourhood hangouts with great drinks, good vibes, and a bit of dancing. Grab your friends and make it a night to remember!
Last updated: July 2025
Embark on a dynamic night out through Windsor’s Chapel Street where every stop amps up the excitement and social buzz. This cocktail bar crawl kicks off at Three Monkeys, a hotspot where infectious energy meets expertly mixed drinks against a backdrop of weekend DJ beats. Next, dive into a playful atmosphere at Better Days Cocktail Bar, where nostalgic video games and inventive cocktails spark shared laughter and lively connections. The journey concludes at Blackwoods Wine & Cocktail Bar, a stylish yet inviting venue blending sophisticated sips with a warm, unpretentious crowd. Together, these venues create a seamless progression from energetic beginnings to an elegant finale—guaranteeing a night packed with fun, flavors, and unforgettable social adventures.
Kicking off the crawl with vibrant energy, Three Monkeys sets the tone with its quirky, intimate vibe and weekend DJ sessions that get the crowd moving. It’s the perfect launchpad for a night of expertly crafted cocktails and lively socializing.
The next stop is a short, easy stroll down Chapel Street, maintaining the crawl’s energetic rhythm with a seamless transition to a playful and inviting atmosphere.
Better Days amps up the social adventure with its fun mix of retro video games, cozy couches, and inventive cocktails—inviting you to engage, compete, and laugh your way through the night.
The next stop is just a quick walk further along Chapel Street, letting you carry forward the lively spirit into a more refined yet equally spirited setting.
Closing out the crawl with sophistication and warmth, Blackwoods offers a curated selection of cocktails and wines in a welcoming space that perfectly balances elegance with an inviting vibe—ideal for reflecting on the night’s adventures.
The next stop is the end of the crawl, concluding the night in style just steps away from Windsor’s buzzing nightlife heart.
This Windsor Cocktail Bar Crawl delivers an exhilarating blend of beats, games, and expertly crafted cocktails that promise to keep your spirits high and your social calendar full. Ready to sip, play, and socialize your way through Chapel Street? Gather your crew and dive into a night where every stop sparks fresh energy and unforgettable moments. Your ultimate Windsor night out awaits—let the adventure begin!
Crawl Map