đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant nightlife with our cocktail bar crawl! Visit three fantastic venues—Ruelle Wine Bar, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering unique drinks, great food, and lively atmosphere. Perfect for wine lovers, cocktail fans, and anyone looking for a fun, memorable evening. Dive into Windsor’s best bars and enjoy a night full of flavor, friends, and good vibes!
Last updated: July 2025
Dive headfirst into Windsor’s spirited cocktail scene with this dynamic bar crawl along Chapel Street. The journey kicks off at Ruelle Wine Bar, where a refined selection of wines and fresh local bites set a sophisticated tone without slowing down the pace. Next, shift gears to Better Days Cocktail Bar—a playground of inventive drinks and nostalgic arcade games that fuels laughter and friendly competition. The grand finale lands at Blackwoods Wine & Cocktail Bar, an effortlessly stylish spot where expertly crafted cocktails and a lively crowd create an unforgettable crescendo to your night. This crawl pulses with energy, blending taste, playfulness, and social adventure into a seamless night out in Windsor.
Kick off the crawl at Ruelle Wine Bar, where carefully curated wines and locally sourced bites offer a polished yet inviting start. It’s the perfect launchpad to gather your crew and ignite the night’s excitement with sophistication and flavor.
The next stop is a short, energizing stroll along Chapel Street, transitioning you from intimate wine elegance to playful cocktail vibes.
Better Days amps up the energy with inventive cocktails and a lively atmosphere packed with retro games and shared fun. This stop invites you to relax into the night’s social adventure, sparking camaraderie and spirited competition.
The next stop is a quick walk down Chapel Street, keeping the buzz alive as you transition to a vibrant cocktail haven.
Finish strong at Blackwoods, where elegant cocktails meet a lively yet unpretentious vibe. This spot serves as the ultimate social hub, perfect for wrapping up the crawl with memorable drinks and animated conversations.
The crawl concludes here, offering a welcoming space to linger and celebrate the night’s highlights.
Ready to turn your night into a whirlwind of flavor, fun, and friendship? This Windsor cocktail bar crawl delivers a seamless progression of experiences—from refined sips to playful games, finishing with stylish cocktails that keep the energy soaring. Gather your crew, explore Chapel Street’s best, and make memories one drink at a time.
Crawl Map