đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant cocktail scene with our exciting bar crawl! Visit 3 fantastic venues — Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar — for a night of delicious drinks, great company, and lively atmosphere. Perfect for foodies and fun-seekers alike, this crawl is your ticket to exploring the best bars, pubs, and restaurants Windsor has to offer. Grab your friends and enjoy a memorable night out!
Last updated: July 2025
Kickstart your night in Windsor with an electrifying cocktail bar crawl that pulses with energy and endless fun. This curated route along Chapel Street weaves through three dynamic hotspots, each delivering a unique flavor and vibe. Begin with Naughty Nancy’s, where live music and hearty bites set an upbeat tone. From there, dive into a playful and social atmosphere at Better Days Cocktail Bar, where inventive drinks meet classic games for a memorable mix of nostalgia and novelty. Finally, wind down in style at Blackwoods Wine & Cocktail Bar, a welcoming space where expert mixology and a refined yet lively ambiance make for the perfect grand finale. This crawl is crafted for adventurers who crave excitement, connection, and expertly crafted cocktails, all within a compact, walkable stretch.
Launching the crawl with high-energy live music and a food-forward cocktail experience, Naughty Nancy’s sets a spirited tone that invites you to dive into Windsor’s lively social scene.
The next stop is a quick stroll down Chapel Street, a vibrant walk that keeps the buzz alive as you head toward a more playful, intimate setting.
This stop shifts gears into a charming realm of games, laughter, and inventive cocktails, making it the perfect social playground to bond and recharge before the final leg.
The next stop is a short, lively walk along Chapel Street, maintaining the crawl’s upbeat momentum as you prepare to indulge in sophisticated sips.
Ending the night with style and expert mixology, Blackwoods offers an elegant yet vibrant atmosphere that blends warmth with class, perfect for wrapping up a spirited adventure.
The crawl concludes here, with Blackwoods serving as the ultimate destination to savor your final cocktails and reflect on an unforgettable night.
Ready to experience Windsor’s cocktail craft like never before? This curated crawl invites you to embrace every moment—whether you’re tapping along to live tunes, battling friends over a game, or savoring a perfectly stirred drink. Grab your crew, plan your route, and let the vibrant energy of Chapel Street guide your night. Each bar promises a distinct chapter in an unforgettable evening of adventure, flavor, and social connection. Cheers to exploring Windsor’s spirited side, one cocktail at a time!
Crawl Map