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, inviting atmospheres, and great food. Perfect for wine lovers, cocktail fans, and anyone looking to explore the best local spots. Whether you're celebrating or just out for fun, this crawl promises an unforgettable night in Windsor’s lively bar scene.
Last updated: July 2025
Get ready to ignite your night in Windsor with a cocktail bar crawl that pulses with energy, creativity, and social spark. This handpicked journey kicks off tucked away at Ruelle Wine Bar, where a sophisticated wine selection and artisanal bites set an elevated tone. From there, shift gears into a playground of nostalgia and craft cocktails at Better Days Cocktail Bar—where classic video games meet inventive drinks, making it impossible not to smile and connect. The grand finale lands at Blackwoods Wine & Cocktail Bar, a welcoming hotspot that effortlessly blends expert mixology with an inviting vibe, perfect for closing out the night with style. Each stop offers a fresh twist on Windsor’s lively nightlife, ensuring your evening flows from chic to spirited and back again in a seamless celebration of flavor and fun.
Ruelle Wine Bar is the perfect launchpad for this crawl, offering a curated wine experience paired with artisan cheeses that awaken your palate and spark anticipation for the night ahead.
The next stop is a short and lively stroll down Chapel Street, keeping the energy buzzing as you approach the more interactive vibes of Better Days Cocktail Bar.
Better Days amps up the fun with its vibrant atmosphere, complete with nostalgic games and inventive cocktails that invite laughter and social connection—an essential energetic pivot in the crawl.
The next stop is just a few minutes’ walk along Chapel Street, a perfect chance to keep the momentum going while soaking in Windsor’s buzzing nightlife buzz.
Blackwoods wraps up the crawl with a polished yet inviting vibe, expertly crafted cocktails, and a space that welcomes both intimate chats and lively group celebrations—ending the night on an elevated, memorable note.
The next stop is the final destination, so take your time to savor the expertly mixed drinks and vibrant energy of Blackwoods as you close out the crawl.
This Windsor cocktail crawl is more than just a night out—it’s a social adventure that evolves with every step, every sip, and every laugh. Whether you’re a cocktail connoisseur or a nightlife explorer, these bars promise a night pulsing with flavor, fun, and unforgettable moments. So rally your crew, map your route, and dive into Windsor’s spirited cocktail scene. Your next great night out starts here.
Crawl Map