đź“… Open Today: Crawl likely open on Fridays
Join our Windsor cocktail bar crawl and explore 5 fantastic venues filled with cozy charm and vibrant energy. From the ship-themed plush couches at Three Monkeys to the plant-filled jungle vibe at Jungle Boy, each spot offers unique cocktails and a friendly atmosphere. Whether you're after rum and cocktails in a snug setting or lively DJ parties on weekends, this crawl promises a fun-filled night in Windsor's coolest hangouts. Perfect for friends looking for a memorable night out!
Last updated: July 2025
Ready to ignite your night in Windsor? This Chapel Street cocktail crawl is a dynamic journey through some of the area’s most spirited bars, each offering a unique pulse to keep the energy flowing. Begin at Three Monkeys, where lively DJ beats and quirky charm set an upbeat tone. Then shift gears to Better Days, blending playful nostalgia with creative cocktails and games that spark connection. Next, elevate your experience at Blackwoods, where sophisticated craft cocktails meet a welcoming crowd, perfect for mingling and moments of delight. The adventure sails on to Holy Grail’s ship-themed sanctuary, a cozy haven where rum reigns supreme amid plush seats and intimate vibes. Finally, plunge into Jungle Boy’s tropical oasis, where exotic drinks in tiki mugs cap off your night with flair and flamboyance. This crawl is not just a sequence of stops but a seamless flow of mood and excitement, crafted for those who crave spirited social adventures and unforgettable tastes.
Kick off the crawl with Three Monkeys’ infectious energy—its vibrant weekend DJ sessions and quirky, snug setup create the perfect launchpad for your night of lively cocktail exploration.
The next stop is just a quick, upbeat stroll down Chapel Street, keeping the night’s momentum alive.
Shift into playful mode at Better Days, where inventive cocktails meet nostalgic gaming fun, energizing your crew with laughter and shared moments in its cozy, game-filled lounge.
The next stop is a short, easy walk along Chapel Street, letting the buzz from Better Days linger as you move forward.
Elevate your evening at Blackwoods, where polished craft cocktails and a curated wine list create an elegant yet inviting vibe that’s perfect for recharging and engaging with fellow night owls.
The next stop is a brief, energizing walk that transitions the vibe toward a vintage-inspired, intimate setting.
Step aboard Holy Grail’s ship-themed haven, where plush seating and a stellar rum selection invite you to savor classic cocktails in an atmosphere that’s both cozy and spirited.
The next stop is a lively short stroll, setting the stage for the crawl’s tropical finale.
Conclude your adventure at Jungle Boy, a tropical oasis pulsing with lush greenery and exotic cocktails served in tiki mugs, delivering a bold, festive finish to your Windsor night.
The next stop is the end of the crawl, leaving you perfectly primed for wherever the night takes you next.
Embrace the vibrant spirit of Windsor with this carefully curated Chapel Street cocktail crawl. Each bar offers a distinct chapter in your night’s story, from rhythmic beats and nostalgic play to elegant sipping and tropical flair. Whether you’re a cocktail connoisseur or a social adventurer, this journey promises unforgettable flavors, lively atmospheres, and new connections. Ready to claim your spot on Windsor’s most thrilling crawl? Grab your crew, bring your curiosity, and let the spirited nights begin!
Crawl Map