đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant nightlife with our cocktail bar crawl! Visit three fantastic venues—Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering unique drinks and great vibes. Perfect for food lovers and cocktail enthusiasts alike, this crawl is your chance to enjoy delicious drinks, lively atmospheres, and a memorable night out in Windsor. Grab your friends and get ready to sip, socialize, and discover the best cocktail spots in town!
Last updated: July 2025
Kick off your night on Windsor’s buzzing Chapel Street with a cocktail crawl that pulses with energy, creativity, and social spark. Begin at Naughty Nancy’s, where the lively pub atmosphere, live music, and hearty food set a dynamic tone. Then shift gears at Better Days Cocktail Bar, a playful hotspot where craft cocktails meet nostalgic board games, creating a fun and interactive vibe. Wrap up your adventure at Blackwoods Wine & Cocktail Bar, where sophisticated mixology and a welcoming ambiance offer the perfect finale to an unforgettable night. This crawl is tailored for those eager to dive deep into Windsor’s spirited cocktail scene, blending vibrant beats, engaging settings, and expertly crafted drinks into one seamless journey.
Launching the crawl with infectious energy, Naughty Nancy’s combines a lively live music scene with bold, food-centric flavors that fuel the night’s momentum from the first sip.
The next stop is a brief stroll along Chapel Street, keeping the buzz alive as you transition into a more playful and intimate cocktail setting.
Better Days shifts the vibe to a quirky, fun-filled space packed with inventive cocktails and nostalgic games, perfect for sparking laughter and friendly competition mid-crawl.
The next stop is a quick, inviting walk that leads you into the elegant yet approachable atmosphere of Blackwoods, setting up the night’s refined finale.
This final stop elevates the night with sophisticated cocktails and a warm, unpretentious ambiance, offering a perfect blend of elegance and energy to close out your Windsor adventure.
The crawl concludes here, with Blackwoods serving as the ultimate spot to savor expertly crafted drinks and reflect on a night well spent.
Ready to own the night on Windsor’s Chapel Street? This cocktail crawl packs a punch from start to finish—melding live music, playful cocktails, and refined sips into an epic social adventure. Whether you’re rallying a crew or diving solo, each stop promises fresh energy and unforgettable flavor. Lace up your walking shoes, bring your best stories, and let Windsor’s cocktail scene show you how to make every hour happy.
Crawl Map