đź“… Open Today: Crawl likely open on Fridays
Explore Windsor's vibrant nightlife with our cocktail bar crawl! Visit three awesome spots—Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering a snug, quirky neighborhood hangout with fantastic cocktails and a lively vibe. Perfect for a fun night out with friends, especially if you're into DJ parties on weekends. Get ready for a night of great drinks, good music, and unforgettable memories in Windsor!
Last updated: July 2025
Kick off an electrifying evening on Windsor’s Chapel Street, where a trio of standout cocktail bars promise a night packed with energy, fun, and unforgettable moments. This crawl is designed to crank up the excitement from the first sip to the last call, weaving through bars that each bring a unique flavor to your night. Begin in the lively, intimate corners of Three Monkeys, where expert cocktails meet weekend DJ sets that get the crowd moving. Then, shift gears to Better Days Cocktail Bar, a playground of playful nostalgia with board games and retro video games, perfect for sparking laughter and camaraderie. Finally, elevate your night at Blackwoods Wine & Cocktail Bar, where classy yet unpretentious vibes and masterful drinks create the perfect finale for this adventurous Windsor crawl. Get ready for a night that’s as dynamic and spirited as the city itself.
Three Monkeys sets the energetic tone of the crawl with its quirky, intimate atmosphere and expertly mixed cocktails, making it the perfect launchpad for a night of social adventure and weekend beats.
The next stop is just a short, lively stroll down Chapel Street, keeping the night’s momentum flowing effortlessly.
Better Days Cocktail Bar injects playful nostalgia into the crawl, with engaging board games and retro video games pairing brilliantly with inventive cocktails to amplify the night’s vibrant energy.
The next stop is a quick hop along Chapel Street, allowing for seamless transitions between each unique atmosphere.
Blackwoods Wine & Cocktail Bar capstones the crawl with its sophisticated yet approachable vibe, offering expertly crafted cocktails and a warm ambiance that invites lingering conversations and celebrations.
The next stop is the perfect conclusion to the crawl, within easy walking distance, ensuring a smooth finish to an exhilarating night.
Wrap up your Windsor cocktail adventure with memories of expertly crafted drinks, contagious energy, and unforgettable social moments. Whether you’re toasting with friends, sparking new connections, or simply indulging in the vibrant Chapel Street nightlife, this crawl delivers a dynamic journey through some of the city’s finest cocktail destinations. Ready to dive in? Gather your crew, bring your sense of adventure, and let Windsor’s spirited cocktail scene show you a fantastic night out.
Crawl Map