đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s coolest cocktail bars on this fun-filled crawl through four unique venues. From the snug, ship-themed Three Monkeys to the eclectic Better Days Cocktail Bar, and the plush Blackwoods Wine & Cocktail Bar to the lively Holy Grail, each spot offers its own quirky charm and fantastic drinks. Whether you're into rum, cocktails, or just a great vibe with DJ parties on weekends, this crawl is the perfect way to explore Windsor’s hidden gems and enjoy a memorable night out with friends.
Last updated: July 2025
Kick off an electrifying night in Windsor’s Chapel Street, where every stop on this cocktail bar crawl serves a fresh burst of energy and flavor. From the infectious rhythms and welcoming buzz of Three Monkeys to the playful, game-fueled atmosphere at Better Days, this adventure sets the perfect stage for meeting new friends and savoring inventive cocktails. As the night builds, Blackwoods offers a refined yet spirited oasis to raise a glass, before culminating at Holy Grail—an atmospheric, ship-inspired retreat where expertly crafted rum cocktails and plush seating invite you to linger and celebrate until the last call. This isn’t just a bar crawl; it’s a dynamic journey through Windsor’s most exciting cocktail scenes.
Launching the crawl with infectious energy, Three Monkeys sets the tone with its quirky vibe and weekend DJ beats, mixing expertly crafted cocktails and a curated beer selection to spark lively conversations and social connections.
The next stop is a short, vibrant stroll down Chapel Street to Better Days, keeping the night’s momentum flowing with its playful, game-centered atmosphere.
Better Days amps up the fun with its nostalgic nod to classic video games and inventive cocktails, creating a spirited backdrop where laughter and friendly competition thrive alongside creative mixology.
The next stop is an easy walk further along Chapel Street to Blackwoods, shifting the vibe toward a more refined yet still vibrant scene.
Blackwoods elevates the night with an elegant mix of expertly crafted cocktails and a curated wine list, offering a lively atmosphere that balances sophistication with an inviting social buzz.
The next stop is a brief, mood-setting walk to Holy Grail, where the night’s adventurous spirit finds a cozy yet dynamic home.
Holy Grail caps the crawl in style with its ship-themed charm, plush seating, and a stellar rum and cocktail menu that invites you to unwind while keeping the night’s energy alive through engaging drinks and convivial vibes.
The next stop is the perfect place to settle in and soak up the final moments of this spirited crawl.
Wrap up your Windsor cocktail adventure with memories of bold flavors, new friendships, and a night that pulses with energy from start to finish. Whether you’re chasing inventive cocktails, lively beats, or cozy corners with character, this crawl captures the essence of Chapel Street’s vibrant nightlife. Ready to take on Windsor’s best bars? Grab your crew, raise your glass, and let the adventure begin!
Crawl Map