đź“… Open Today: Crawl likely open on Fridays
Join us in Windsor for an unforgettable cocktail bar crawl! Visit three fantastic venues—Ruelle Wine Bar, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering a unique vibe, delicious drinks, and great food. Perfect for wine lovers, cocktail fans, or anyone looking to enjoy a lively night out with friends. Discover local favorites and sip your way through Windsor’s best bars in one epic evening!
Last updated: July 2025
Get ready to ignite your night across Windsor’s dynamic cocktail landscape. This adventure starts in the intimate charm of Ruelle Wine Bar, where handpicked wines and fresh gourmet pairings set a sophisticated tone. Next, the energy ramps up as you step into Better Days Cocktail Bar, a playground of inventive cocktails, nostalgic games, and vibrant social buzz. Finally, the crawl lands at Blackwoods Wine & Cocktail Bar, where polished mixology meets a warm, buzzing atmosphere — perfect for wrapping up the evening with friends or sparking new connections. This isn’t just a bar crawl; it’s a curated experience that pulses with excitement, variety, and the true spirit of Windsor’s nightlife.
Kick off your crawl at Ruelle Wine Bar, where refined wine selections and artisanal nibbles invite you into an elegant yet inviting setting, laying the groundwork for an adventurous night ahead.
The next stop is a short, lively stroll along Windsor’s iconic Chapel Street, perfect for soaking in the buzz as you head toward spirited cocktails and playful vibes.
At Better Days, the energy surges with playful cocktails and a nostalgic mix of board and video games, transforming the night into a social playground where laughter and fun flow freely.
The next stop is a quick, vibrant walk down Chapel Street, keeping the momentum alive as you approach a stylish spot known for its expert mixology and lively atmosphere.
Blackwoods rounds out the crawl with polished cocktails and a buzzing yet approachable ambiance, delivering a perfect blend of sophistication and spirited energy to cap off your Windsor night.
The crawl concludes here, so your journey wraps up with ease in this vibrant hub, leaving you perfectly placed to continue the evening or reflect on the adventure.
Your Windsor Cocktail Bar Crawl is more than a night out — it’s a journey through diverse flavors, atmospheres, and unforgettable moments. Whether you’re savoring exquisite wines, challenging friends to a game while sipping creative concoctions, or soaking up the vibrant energy of expertly crafted cocktails, this crawl delivers excitement at every turn. Lace up your walking shoes, gather your crew, and dive headfirst into Windsor’s lively nightlife scene. The best night you’ve had in a while is just a sip away.
Crawl Map