đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant cocktail scene with our exclusive bar crawl! Visit three fantastic venues—Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering unique drinks and lively atmospheres. Perfect for food lovers and cocktail enthusiasts alike, this crawl combines great food, creative cocktails, and fantastic company. Whether you're celebrating or just looking for a fun night out, our Windsor cocktail crawl promises an unforgettable evening of sips, laughs, and memories!
Last updated: July 2025
Kick off your Windsor night with a cocktail bar crawl that pulses with energy, creativity, and social buzz along Chapel Street. This trio of standout bars delivers an electrifying journey through the best of Windsor’s mixology scene. From the infectious rhythms and hearty bites at Naughty Nancy’s to the nostalgic board games and inventive drinks at Better Days, you’ll find every moment packed with excitement. Cap off your adventure at Blackwoods Wine & Cocktail Bar, where polished cocktails meet a welcoming ambiance—perfect for closing the night on a high note. Each stop offers a fresh vibe and experience, ensuring your crawl flows naturally from upbeat beginnings to a stylish finale.
Launch your crawl in this lively pub where infectious live music and bold craft cocktails set a vibrant tone. Naughty Nancy’s combines rich flavors and a buzzing atmosphere, making it the perfect energetic starting point to ignite your night.
The next stop is a short, easy stroll along Chapel Street, keeping the momentum alive as you head towards a spot blending fun and flair.
This is where playful nostalgia meets inventive mixology. Better Days amps up the social vibes with cozy couches, classic video games, and creative cocktails, making it a lively hub to share laughs and elevate the fun mid-crawl.
The next stop is a quick walk down Chapel Street, perfectly timed to keep your energy buzzing as you step into a sleek and sophisticated finale.
Finish strong in this refined yet inviting bar where expert cocktails and a curated wine list create a polished atmosphere. Blackwoods offers the perfect balance of excitement and elegance, wrapping up your adventurous crawl with style.
The next stop is the conclusion of your crawl, ideal for savoring your last sips without needing to walk further.
Your Windsor cocktail bar crawl is a dynamic journey through the city’s most vibrant and charismatic drinking destinations. Each bar brings a fresh wave of energy, from live music and hearty bites to playful nostalgia and sophisticated mixology. Whether you’re celebrating with friends or sparking new connections, this crawl ensures a night packed with excitement and unforgettable moments. Ready to explore Windsor’s cocktail scene like never before? Gather your crew and let the adventure begin!
Crawl Map