đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant nightlife with our exclusive cocktail bar crawl! Visit three fantastic venues—Ruelle Wine Bar, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering unique drinks, lively atmospheres, and great vibes. Perfect for a night out with friends, exploring the best wine bars, cocktail spots, and event venues in town. Cheers to a memorable evening of sipping, socialising, and fun!
Last updated: July 2025
Kick off your night in Windsor with a cocktail bar crawl designed to ignite your senses and fuel your social spirit. Begin with Ruelle Wine Bar’s handpicked wines and artisanal bites, setting a sophisticated tone that primes your palate for adventure. Next, step into Better Days Cocktail Bar where the energy cranks up with playful board games, retro video games, and inventive cocktails that spark laughter and connection. Conclude your journey at Blackwoods Wine & Cocktail Bar, an elegant yet energetic venue where masterful mixology meets a vibrant crowd, sealing the night with unforgettable flavors and lively camaraderie. This crawl weaves a seamless experience of evolving vibes, from refined to playful to spirited — perfect for those craving a night packed with excitement and crafted libations.
Ruelle Wine Bar sets the tone for the evening with its curated wine selection and gourmet pairings, offering a chic and inviting start to the crawl that sharpens your taste buds and sparks engaging conversation.
The next stop is a lively 7-minute stroll down Chapel Street, shifting the vibe from elegant wine sophistication to playful cocktail creativity.
Better Days infuses the night with upbeat energy and interactive fun, thanks to its retro games and inventive cocktails—perfect for amplifying social vibes and laughter before the final leg.
The next stop is a short 3-minute walk along Chapel Street, guiding you toward a bustling hotspot that blends refined drinks with vibrant energy.
Blackwoods rounds out the crawl with a masterclass in cocktail craft and warm, buzzing atmosphere, offering a perfect finale where lively crowds and expert mixology create an unforgettable nightcap experience.
The next stop is the conclusion of the crawl, placing you at the heart of Windsor’s spirited nightlife scene.
Wrap up your Windsor cocktail adventure with a night full of bold flavors, vibrant energy, and new connections. Whether celebrating milestones or simply chasing great drinks and good company, this crawl delivers an electrifying social experience you’ll be eager to relive. Ready your taste buds, gather your crew, and let Windsor’s cocktail bars show you how to turn an evening out into an epic adventure.
Crawl Map