đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant cocktail scene with this fun-filled bar crawl! Visit three fantastic venues—Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering unique drinks and great vibes. Perfect for food lovers and cocktail enthusiasts alike, this crawl combines food-centric pub atmospheres with expertly crafted cocktails. Whether you're celebrating or just out for a good time, enjoy a memorable night exploring Windsor’s best bars and restaurants in one epic evening!
Last updated: July 2025
Dive into the heart of Windsor’s nightlife with a cocktail bar crawl designed for those who crave a night packed with flavor, fun, and unforgettable social energy. Starting strong at Naughty Nancy’s, you’ll be swept up by live music and a food-centric atmosphere that sets a vibrant tone. Next, step into Better Days Cocktail Bar where nostalgia meets inventive mixology, offering a playful twist with board games and retro video games that spark laughter and connection. Finally, wind down with style at Blackwoods Wine & Cocktail Bar, where expert-crafted drinks meet an elegantly inviting ambiance, perfect for toasting new friends or deepening conversations. This crawl’s energetic flow takes you on a seamless journey through Windsor’s hottest cocktail destinations — each stop building on the last for an adventurous night that never loses momentum.
Kick off the night at Naughty Nancy’s, where lively live music and a vibrant crowd create an electric atmosphere. This food-driven pub fuels the evening with hearty dishes and craft cocktails that bring a bold start to the crawl’s high-energy adventure.
The next stop is a brief, easy stroll along Chapel Street, keeping the momentum alive as you head toward a spot that amps up the fun with games and creative cocktails.
Better Days shifts the vibe to playful and social, blending inventive cocktails with nostalgic video and board games. It’s the perfect spot to share laughs, spark friendly competition, and keep the night buzzing with warmth and charm.
The next stop is just a short walk down Chapel Street, offering a smooth transition to a more refined yet lively scene to elevate your cocktail experience.
Conclude your crawl at Blackwoods, where the energy matures into a sophisticated buzz. Expert cocktails and a curated wine list create an elegant yet approachable atmosphere, ideal for celebrating the night’s adventures with style and camaraderie.
The next stop is the final destination, so no walking needed—just settle in and savor the last sips of an unforgettable night.
This Windsor cocktail bar crawl is your passport to an evening packed with vibrant energy, creative flavors, and social thrills. From live music-fueled beginnings to playful mid-crawl antics and a polished finale, the night is crafted to keep your spirits high and your glass full. Gather your crew, bring your adventurous spirit, and let Chapel Street’s best cocktail venues take you on a spirited journey you won’t forget. Cheers to the ultimate Windsor night out!
Crawl Map