đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant cocktail scene with our exclusive 3-venue crawl! Sip creative cocktails at Three Monkeys, enjoy the cozy vibes at Better Days Cocktail Bar, and unwind at Blackwoods Wine & Cocktail Bar. From snug neighborhoods to lively DJ parties on weekends, this crawl is perfect for anyone looking to discover hidden gems and enjoy a night of great drinks, good music, and unforgettable fun in Windsor.
Last updated: July 2025
Kickstart your night in Windsor with an adrenaline-pumped cocktail bar crawl designed to ignite your senses and spark social adventures. This curated journey through Chapel Street’s top cocktail spots offers a perfect blend of intimate charm, playful energy, and sophisticated buzz. From the upbeat rhythms and welcoming quirks of Three Monkeys to the nostalgic, game-fueled joy at Better Days Cocktail Bar, culminating in the polished yet inviting elegance of Blackwoods Wine & Cocktail Bar, each stop elevates your experience. Ready your taste buds and your crew for a night where every sip and step brings new excitement.
Opening the night with infectious energy, Three Monkeys sets the tone with its quirky charm and weekend DJ beats that invite you to dive into the crawl with expertly mixed cocktails and a buzzy atmosphere that sparks instant connection.
The next stop is a brief, lively stroll along Chapel Street that keeps the night’s momentum flowing as you head to Better Days Cocktail Bar.
Injecting a playful twist into the evening, Better Days Cocktail Bar offers a vibrant social playground with nostalgic video games and inventive cocktails—perfect for sharing laughs and sparking friendly competition that lifts the night’s vibe.
The next stop is a short, energetic walk that maintains the night’s upbeat rhythm, leading you to the refined yet spirited atmosphere of Blackwoods Wine & Cocktail Bar.
Capping off the crawl, Blackwoods Wine & Cocktail Bar blends sophistication with welcoming warmth, delivering expertly crafted cocktails and a lively scene that invites you to savor the night’s final moments in style and social buzz.
The next stop is the perfect moment to reflect and unwind as this is the final destination of the crawl.
Celebrate Windsor’s vibrant cocktail culture by conquering this spirited bar crawl — where every venue offers its own flavor of excitement and social energy. Whether you're mixing with locals, competing over classic games, or savoring masterful drinks, this journey promises an unforgettable night packed with thrills and new connections. Ready your crew and dive into Windsor’s most exhilarating cocktail adventure!
Crawl Map