đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s best cocktail scene with our vibrant bar crawl featuring three fantastic venues: Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Perfect for foodies and drink lovers alike, this pub crawl takes you through a mix of stylish bars, cozy pubs, and lively event venues. Sip handcrafted cocktails, enjoy great vibes, and make new friends along the way. Whether you're celebrating or just looking for a fun night out, this crawl is your ticket to Windsor’s top drinking spots!
Last updated: July 2025
Dive headfirst into Windsor’s buzzing nightlife with this exhilarating cocktail bar crawl that masterfully blends bold flavors, playful energy, and sophisticated sips. Your adventure kicks off at Naughty Nancy’s, where the infectious buzz of live music and hearty, flavor-packed dishes prime your palate and set the night’s lively tone. From there, the vibe shifts to a spirited playground at Better Days Cocktail Bar, where inventive drinks meet a nostalgia-fueled atmosphere filled with classic board and video games—a perfect spot to spark laughter and friendly competition. Finally, the crawl winds down at Blackwoods Wine & Cocktail Bar, striking the perfect balance between energetic and elegant with expertly crafted cocktails and a welcoming ambiance that invites connection and celebration. This curated journey ensures every step pulses with excitement and every stop offers a fresh layer to your Windsor night out.
Launching your night at Naughty Nancy’s sets the pace with a vibrant mix of live music, craft cocktails, and hearty bites that fuel your energy and ignite the social buzz.
The next stop is just a short, lively stroll down Chapel Street, keeping the momentum alive as you head to a bar that blends nostalgia with spirited fun.
Better Days amps up the crawl with a playful ambiance and inventive cocktails, inviting you to dive into classic games and share laughs that keep the night adventurous and interactive.
The next stop is a quick walk further along Chapel Street, shifting the vibe toward a more polished and refined cocktail experience.
Conclude the crawl at Blackwoods, where sleek sophistication meets vibrant energy in expertly crafted cocktails and a welcoming setting that celebrates connection and good times.
The crawl ends here, right in the heart of Chapel Street’s vibrant scene—perfect for lingering or planning your next adventure.
Cap off your Windsor cocktail bar crawl with memories of lively tunes, playful competition, and exquisite drinks that only Chapel Street can deliver. Whether you’re raising a glass with friends or making new ones along the way, this spirited route promises a night packed with excitement and social adventure. Ready to take on Windsor’s nightlife? Grab your crew, hit the pavement, and let the good times roll!
Crawl Map