đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's hidden gem cocktail bars on this lively crawl! Visit three quirky venues—Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—and enjoy a mix of snug atmospheres, unique drinks, and weekend DJ parties. Perfect for those who love a relaxed yet vibrant night out with friends, good vibes, and great cocktails. Get ready to explore Windsor’s best kept secret hangouts and make some unforgettable memories!
Last updated: July 2025
Dive into Windsor’s buzzing cocktail scene with a carefully curated bar crawl that promises more than just drinks—it’s a full-on social adventure. Begin your night at Three Monkeys, where quirky charm meets infectious energy, setting the perfect tone with its lively DJ sessions and expertly crafted cocktails. Next, amp up the fun at Better Days Cocktail Bar, where nostalgia, games, and inventive concoctions create a playground for friends and fellow cocktail lovers. Finally, wind down with a sophisticated yet warmly inviting atmosphere at Blackwoods Wine & Cocktail Bar, where impeccable cocktails and a curated wine list bring the night to an elegant climax. This crawl offers a seamless flow of excitement, socializing, and craft mastery, making Windsor’s nightlife unforgettable.
Kick off your evening at Three Monkeys, a vibrant spot where lively beats, quirky decor, and top-notch cocktails ignite the night’s energy and get the social vibe flowing.
The next stop is a short stroll down Chapel Street, keeping the momentum high and the buzz alive as you head to your next playful destination.
Step into Better Days Cocktail Bar for a spirited mix of nostalgic gaming fun and inventive cocktails, elevating the night with laughter, friendly competition, and creative sips.
The next stop is a quick walk along Chapel Street, offering a seamless transition to a more refined cocktail experience.
Conclude the crawl at Blackwoods, where the energy softens into an elegant vibe filled with expertly crafted cocktails and a welcoming atmosphere that turns the night into a memorable celebration.
The next stop is the perfect chance to savor the moment or continue your adventure elsewhere in Windsor’s lively nightlife.
Wrap up your Windsor Cocktail Bar Crawl with a sense of accomplishment and buzz-worthy memories. Whether you’re toasting new friendships, celebrating milestones, or simply chasing the thrill of expertly mixed drinks and vibrant social scenes, this crawl delivers a dynamic night you won’t forget. Ready to take on Windsor’s spirited nightlife? Grab your crew, set your pace, and let the adventure begin!
Crawl Map