đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s best cocktail bars on this fun-filled crawl! Visit three fantastic venues—Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering unique drinks and vibrant atmospheres. Perfect for foodies and cocktail lovers alike, this pub crawl combines great spirits, tasty bites, and lively vibes across prime food-centric spots, pubs, and event venues. Gather your friends and sip your way through Windsor's bustling bar scene!
Last updated: July 2025
Get ready for an electrifying night out in Windsor’s buzzing Chapel Street with this curated cocktail bar crawl designed for thrill-seekers and social butterflies alike. Kick off your adventure at Naughty Nancy’s, where live bands and bold flavors fuel a high-energy atmosphere perfect for sparking connections. Then, shift gears at Better Days Cocktail Bar — a playful hotspot where inventive cocktails meet classic video games, turning every sip into a shared celebration. Finally, wind down the evening with style at Blackwoods Wine & Cocktail Bar, a chic yet inviting spot offering expertly crafted cocktails and an atmosphere that balances spirited fun with sophisticated ease. This crawl is your ticket to discovering Windsor’s dynamic nightlife scene, blending diverse vibes into one seamless journey of flavor, fun, and unforgettable moments.
Launching your crawl here means diving straight into Windsor’s dynamic nightlife with Naughty Nancy’s spirited live music and robust, flavor-packed menu – a perfect launchpad for high-energy socializing.
The next stop is a brief, lively stroll down Chapel Street, allowing you to soak in Windsor’s vibrant street scene as you head toward your next cocktail adventure.
Better Days Cocktail Bar amps up the fun with its inventive drinks and interactive gaming vibe, turning your evening into an engaging mix of playful competition and crafted cocktail excellence.
The next stop is just a short walk further along Chapel Street, keeping the momentum alive as you venture into the final phase of your crawl.
Closing out the crawl, Blackwoods offers a refined yet lively atmosphere with top-tier cocktails and a warm ambiance, perfect for wrapping up your night with style and spirited conversations.
The next stop is the conclusion of the crawl, so you can relax and savor the moment without any more walking.
Whether you’re a local or just passing through, this Windsor cocktail bar crawl offers an unforgettable blend of music, games, and expertly crafted drinks that guarantee an energetic night full of new friendships and lasting memories. So gather your crew, bring your appetite for adventure, and explore the best of Chapel Street’s cocktail scene — your ultimate night out awaits!
Crawl Map