đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant nightlife with our cocktail bar crawl! Visit three fantastic spots — Ruelle Wine Bar, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar — each offering unique drinks, lively atmospheres, and great food. Whether you’re into craft cocktails, fine wines, or just looking for a fun night out, this crawl is perfect for friends looking to sip, socialize, and discover Windsor’s best bars. Cheers to a memorable evening!
Last updated: July 2025
Kick off your night in Windsor with a cocktail crawl that masterfully blends sophistication, fun, and social adventure. Starting at Ruelle Wine Bar, immerse yourself in a world of finely curated wines and artisan bites that set an intimate yet energizing tone. From there, shift gears to Better Days Cocktail Bar where nostalgia meets inventive mixology, amplified by playful games and lively camaraderie. Conclude your journey at Blackwoods Wine & Cocktail Bar, where expertly crafted cocktails and a breezy, inviting atmosphere create the perfect crescendo. This crawl is designed to keep the pulse rising, delivering diverse experiences that flow effortlessly from one unforgettable stop to the next.
Set the tone of your evening at Ruelle Wine Bar, where a refined selection of wines and gourmet pairings create a sophisticated yet approachable start to your cocktail adventure.
The next stop is a short and lively walk along Chapel Street that transitions you from elegant sips to playful and vibrant cocktail antics at Better Days.
Inject energy and fun into your night at Better Days, where throwback vibes, interactive games, and inventive cocktails create a magnetic social hotspot that ramps up the excitement.
The next stop is a quick stroll further down Chapel Street, allowing your night to flow naturally into an elegant yet spirited finale at Blackwoods.
Cap off your crawl at Blackwoods, where a polished yet unpretentious atmosphere and expertly crafted drinks offer the perfect space to celebrate, connect, and keep the good times rolling.
The next stop is the end of the crawl, leaving you perfectly positioned to explore Windsor’s nightlife or continue your night with newfound friends.
This Windsor cocktail bar crawl is your passport to a night filled with inventive drinks, vibrant social scenes, and seamless energy shifts. Whether you’re a cocktail connoisseur or an adventurous spirit, this journey through Ruelle, Better Days, and Blackwoods promises memorable moments and new connections. Ready to raise your glass and explore Windsor’s spirited pulse? Gather your crew and dive in — the night is yours to own.
Crawl Map