đź“… Open Today: Crawl likely open on Fridays
Ready for a night of fun in Windsor? Our cocktail bar crawl takes you through 3 fantastic venues: Ruelle Wine Bar, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Whether you love craft cocktails, fine wine, or just a great atmosphere, this crawl has it all. Perfect for friends looking to explore the best of Windsor’s bar scene, enjoy delicious drinks, and make some memories. Let’s toast to a night you won’t forget!
Last updated: July 2025
Kick off your Windsor night with a cocktail bar crawl that pulses with energy, flavor, and social spark. Begin at Ruelle Wine Bar, where a refined wine selection and gourmet pairings set the tone for a night of discovery. From there, the atmosphere shifts to playful and bold at Better Days Cocktail Bar — a lively hub blending creative cocktails with nostalgic gaming fun. Finally, wrap up your adventure at Blackwoods Wine & Cocktail Bar, where expert mixology meets an inviting buzz, perfect for toasting the night's stories. This crawl is designed to keep the excitement building, the drinks flowing, and the connections thriving along Chapel Street’s vibrant scene.
Ruelle Wine Bar is the perfect launchpad for your crawl, offering a sharp focus on premium wines and locally sourced bites that awaken your palate and set an elevated tone for the evening.
The next stop is a short, lively stroll along Chapel Street, shifting the energy from refined wine tasting to vibrant cocktail fun.
Better Days infuses the night with playful energy—think inventive, hand-crafted cocktails paired with a nostalgic gaming twist that amps up the social vibe and invites shared laughter.
The next stop is just a brisk walk down Chapel Street, where the mood turns even more dynamic and the cocktails get bolder.
Blackwoods delivers the grand finale, blending expertly mixed cocktails and a lively atmosphere that keeps the night buzzing—ideal for closing out your adventure with style and spirited conversation.
The next stop is the conclusion of the crawl, with Blackwoods perfectly placed to cap off the night’s unfolding excitement.
This Windsor Cocktail Bar Crawl offers more than just drinks—it’s a carefully crafted journey through distinctive atmospheres and top-tier libations. Whether you’re a wine aficionado, a cocktail enthusiast, or just chasing a night full of energy and connection, this Chapel Street adventure promises memorable moments and vibrant vibes. Ready to ignite your night? Grab your crew, hit the pavement, and let Windsor’s spirited cocktail scene elevate your evening.
Crawl Map