đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant cocktail scene with our curated bar crawl! Visit three fantastic venues—Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering unique drinks, lively atmospheres, and great vibes. Perfect for anyone looking to enjoy a fun night out with friends, indulge in craft cocktails, and discover hidden gems in the town’s food-centric pub and bar scene. Cheers to unforgettable evenings in Windsor!
Last updated: July 2025
Dive into Windsor’s Chapel Street for a cocktail adventure that pulses with energy and excitement. Kick off your night at Naughty Nancy’s, where hearty food meets live music in a bustling, vibrant pub setting that instantly lifts your spirits. From there, the crawl steps into a playful realm at Better Days Cocktail Bar—think inventive drinks, cozy couches, and a throwback arcade atmosphere perfect for shared laughs and new memories. Finally, wind down (but not slow down) at Blackwoods Wine & Cocktail Bar, where expertly crafted cocktails and a welcoming yet sophisticated vibe invite you to linger and soak up the night’s last exhilarating moments. This crawl isn’t just about drinks; it’s a dynamic journey through Windsor’s spirited social scene.
Kickstart your crawl with Naughty Nancy’s electric atmosphere—where live tunes, bold cocktails, and vibrant pub energy set the perfect tone for an adventurous night ahead.
The next stop is a quick, lively stroll along Chapel Street, keeping the buzz alive as you head towards the playful charm of Better Days Cocktail Bar.
Step into a world where nostalgia meets craft cocktails—Better Days offers a spirited mix of fun games, inventive drinks, and a welcoming vibe that fuels engaging social moments.
The next stop is just a short walk down Chapel Street, smoothly shifting your adventure towards the sophisticated yet inviting ambiance of Blackwoods Wine & Cocktail Bar.
Cap off your crawl in style at Blackwoods, where elegant cocktails and a warm, unpretentious setting create the ultimate hangout spot to celebrate the night’s unforgettable flow.
The next stop is the conclusion of the crawl, leaving you perfectly positioned to either continue your night in Windsor or savor the memories made.
From bold beginnings to playful middle stops and a classy finale, this Windsor cocktail crawl is designed to fuel your night with nonstop energy, exciting flavors, and social sparks. Grab your crew, pace yourself through these distinct vibes, and turn Chapel Street into your personal playground of cocktails and camaraderie. Ready to raise your glass to Windsor’s liveliest bar adventure? Let’s get this crawl started!
Crawl Map