đź“… Open Today: Crawl likely open on Fridays
Explore Windsor's vibrant cocktail scene with our curated bar crawl! Visit three fantastic venues — Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar — each offering a snug, quirky vibe perfect for a laid-back night or weekend DJ parties. Whether you're into creative cocktails, cozy hangouts, or lively DJ nights, this crawl promises a memorable evening in Windsor’s coolest neighborhood. Grab your friends and get ready to toast at these top spots!
Last updated: July 2025
Get ready to ignite your night in Windsor with a cocktail bar crawl that pulses with energy, creativity, and social buzz. This carefully curated route along Chapel Street kicks off with Three Monkeys, where upbeat tunes and expert mixology set the tone for a night of spirited adventure. Next, slide into Better Days Cocktail Bar’s playful den, where nostalgic gaming meets inventive drinks, elevating the excitement and sparking fresh connections. Finally, round out your journey at Blackwoods Wine & Cocktail Bar, where a refined yet lively atmosphere welcomes you to celebrate the perfect nightcap. From rhythmic beats to playful competition and elegant sips, this crawl delivers a dynamic night out that keeps your spirits high and your conversations flowing.
Launching your crawl at Three Monkeys sets an infectious pace with its vibrant weekend DJ sessions and expertly crafted cocktails that energize the crowd. This spot’s quirky yet welcoming character sparks immediate social connections and primes you for the night ahead.
The next stop is a brief, lively stroll down Chapel Street, keeping the momentum flowing as you head to Better Days Cocktail Bar.
Better Days amps up the fun factor with its engaging blend of retro video games, cozy seating, and innovative cocktails. This stop invites playful competition and shared laughter, injecting a dynamic social energy that contrasts delightfully with the crawl’s kickoff.
The next stop is just a quick walk further along Chapel Street, keeping you in the heart of Windsor’s buzzing nightlife scene as you head to Blackwoods Wine & Cocktail Bar.
Closing out your crawl at Blackwoods brings a sophisticated yet lively vibe, balancing elegance with a social buzz. Its expert cocktails and curated wine list provide the perfect stage for deep conversations and celebratory toasts, making it an unforgettable finale.
The crawl concludes here, offering a comfortable spot to linger and soak up Windsor’s vibrant late-night atmosphere.
This Windsor Cocktail Bar Crawl is your passport to an unforgettable night packed with flavor, fun, and connection. Whether you’re sparking new friendships, igniting old ones, or simply chasing the perfect cocktail, these Chapel Street gems deliver a seamless journey of energy and excitement. So grab your crew, pace yourselves, and toast to a night that’s as lively and adventurous as Windsor itself. Ready, set, sip!
Crawl Map