đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant cocktail scene with our exclusive bar crawl! Explore three fantastic venues: Ruelle Wine Bar, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Perfect for cocktail lovers, wine enthusiasts, and anyone looking for a fun night out. Enjoy delicious drinks, lively atmosphere, and great company as you hop between these top-notch spots. Whether you're celebrating or just craving a memorable evening, this crawl promises an unforgettable experience in Windsor!
Last updated: July 2025
Embark on a spirited journey through Windsor’s cocktail hotspots where every stop redefines your night out. Begin amid the curated elegance of Ruelle Wine Bar, where exquisite wines and artisanal pairings set the tone for an evening of discovery. Next, shift gears at Better Days Cocktail Bar, a lively playground blending inventive drinks with nostalgic board games and retro video gaming, sparking laughter and connection. Finally, elevate the experience at Blackwoods Wine & Cocktail Bar, where polished mixology meets an inviting atmosphere, perfect for closing the crawl with style. This crawl blends refined tastes, playful energy, and social buzz into one seamless, exhilarating night in Windsor.
Kick off your crawl at Ruelle Wine Bar, where a sophisticated selection of wines and fresh local bites provide a refined launching pad that sharpens your palate and sets a classy tone for what’s to come.
The next stop is a short and lively stroll to Better Days Cocktail Bar, keeping the momentum going with an upbeat shift from wine to inventive cocktails.
Inject playful energy into the night at Better Days, where creative cocktails collide with retro gaming and cozy corners, sparking spontaneous fun and social buzz just a heartbeat away from Windsor’s main drag.
The next stop is a brief, vibrant walk along Chapel Street to Blackwoods Wine & Cocktail Bar, transitioning smoothly into an elegant yet inviting scene.
Conclude your crawl at Blackwoods, where expert mixologists serve up polished cocktails in a lively yet sophisticated setting, perfect for toasting the night’s adventures and making lasting memories.
The next stop is the end of the crawl, leaving you perfectly positioned to continue your evening in Windsor or savor the nightcap here.
Your Windsor cocktail adventure doesn’t just end with great drinks—it’s a celebration of discovery, camaraderie, and the city’s vibrant nightlife spirit. Whether you’re raising a glass with friends or meeting new faces along the way, this crawl offers the perfect blend of style, fun, and unforgettable moments. Ready to dive in? Lace up your walking shoes, bring your sense of adventure, and let Windsor’s cocktail scene show you a night you’ll be talking about for weeks.
Crawl Map