đź“… Open Today: Crawl likely open on Fridays
Explore Windsor's vibrant cocktail scene with our curated bar crawl! Visit five fantastic venues including Three Monkeys, Better Days Cocktail Bar, Blackwoods Wine & Cocktail Bar, Holy Grail, and Jungle Boy. From ship-themed cozy spots with plush couches to plant-filled lounges serving tiki mugs, there's something for every cocktail lover. Enjoy a mix of quirky neighbourhood hangouts, rum and cocktails, and weekend DJ parties. Perfect for an unforgettable night out with friends in Windsor!
Last updated: July 2025
Set your evening ablaze on Windsor’s iconic Chapel Street with this high-energy cocktail bar crawl that promises an unforgettable social adventure. Each stop pulses with its own unique flavor—from the quirky, music-driven buzz of Three Monkeys to the playful and nostalgic atmosphere at Better Days Cocktail Bar. As you weave through intimate, expertly crafted spaces like Blackwoods and Holy Grail, the night builds momentum, culminating in the vibrant, tropical charm of Jungle Boy. Expect inventive cocktails, lively crowds, and a seamless vibe progression that keeps the excitement flowing and the good times rolling.
Launch your night at Three Monkeys, where an eclectic mix of quirky décor and pulsing weekend DJ sets creates an energetic yet intimate atmosphere, setting the perfect tone for the crawl’s unfolding adventure.
The next stop is a quick, vibrant stroll down Chapel Street, keeping the energy flowing as you head towards Better Days Cocktail Bar.
Better Days injects playful nostalgia with its classic video games and inventive cocktails, elevating the crawl’s social spirit and inviting fun, competitive moments among friends before the night intensifies.
The next stop is a short walk along Chapel Street, maintaining the lively momentum as you approach the sophisticated vibe of Blackwoods Wine & Cocktail Bar.
Blackwoods offers a refined yet vibrant mid-crawl experience, where expertly crafted cocktails and a curated wine list create an elegant contrast that refreshes and elevates the night’s pace.
The next stop is a brief, engaging stroll that leads you deeper into Chapel Street’s energetic heart, arriving at the cozy, themed Holy Grail.
Holy Grail’s ship-inspired interior and expertly made rum cocktails offer a rich, immersive experience that balances lively group vibes with intimate comfort, steering the crawl toward an inviting climax.
The next stop is a lively walk just a few doors down, perfect for keeping up the social buzz as you enter the tropical oasis of Jungle Boy.
Jungle Boy caps off the crawl with a burst of tropical energy—lush greenery, exotic tiki cocktails, and a buzzing lounge atmosphere transform the night into an adventurous escapade bursting with flavor and flair.
The crawl concludes here, leaving you perfectly poised to either continue the night or savor the memories of a cocktail journey well traveled.
This Windsor cocktail bar crawl invites you to embrace every twist and turn of Chapel Street’s vibrant nightlife. From quirky beats and nostalgic games to sophisticated sips and tropical escapes, each stop fuels the next, crafting a night packed with excitement and connection. Ready to rally your crew and dive into a whirlwind of bold flavors and lively scenes? Let this adventure be the spark that ignites your next unforgettable evening in Windsor.
Crawl Map