đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant cocktail scene with our fun-packed crawl through three unique venues: Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Whether you're after quirky neighbourhood hangouts, expertly crafted cocktails, or lively DJ parties on weekends, this crawl has it all. Perfect for a night out with friends, enjoy the friendly atmosphere, creative drinks, and unforgettable memories in the heart of Windsor’s coolest spots.
Last updated: July 2025
Kick off your night in Windsor with a cocktail crawl that pulses with energy, personality, and inventive flavors. Begin at Three Monkeys, where quirky charm meets weekend DJ sets, setting a dynamic tone to ignite your evening. As the night unfolds, Better Days Cocktail Bar invites you to unleash your playful side with nostalgic video games and crafty cocktails, blending social buzz with a splash of fun. Finally, settle into the sophisticated yet inviting atmosphere of Blackwoods Wine & Cocktail Bar, where expertly mixed drinks and attentive service perfect the night’s crescendo. This crawl is a curated adventure through Windsor’s vibrant cocktail culture—each stop building momentum, offering fresh vibes, and connecting you with the city’s spirited nightlife.
Launch your evening here where infectious energy and rhythmic DJ sessions set the perfect vibrant backdrop for adventurous cocktail tasting and lively socializing.
The next stop is a short, energetic stroll down Chapel Street, keeping the momentum alive as you head toward a more playful and interactive vibe.
This spot shifts the scene with nostalgic flair, combining inventive cocktails with a spirited gaming atmosphere that sparks connection and laughter among friends old and new.
The next stop is a brisk walk along Chapel Street, a seamless transition toward a refined yet lively finale.
Conclude your crawl at this elegant haven where masterfully crafted cocktails and a warm, inviting vibe bring your vibrant night to a memorable close.
The next stop is the perfect point to either extend your night out nearby or reflect on an unforgettable cocktail adventure.
Ready to embrace Windsor’s cocktail culture with a night full of energy, flavor, and social thrills? This crawl promises a curated journey through distinct atmospheres and craft concoctions that keep the buzz alive from start to finish. Grab your crew, pace yourself, and let Windsor’s spirited bars take you on an unforgettable adventure. Cheers to the night ahead!
Crawl Map