đź“… Open Today: Crawl likely open on Fridays
Experience the best of Windsor’s cocktail scene with our lively bar crawl featuring three fantastic venues: Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Perfect for food-loving drinkers, this crawl combines great drinks, vibrant atmospheres, and a touch of fun. Whether you're after creative cocktails, cozy vibes, or wine and spirits, these spots deliver. Gather your friends and make unforgettable memories exploring Windsor's top food-centric bars and pubs in one epic night out.
Last updated: July 2025
Embark on an exhilarating evening through Windsor’s Chapel Street, where each stop amps up the night’s energy and flavor. This cocktail bar crawl bursts to life at Naughty Nancy’s, a lively pub pulsing with live music and mouthwatering dishes that fuel your fun. Next, step into Better Days Cocktail Bar’s nostalgic playground, where inventive drinks meet playful vibes and social games spark laughter. Finally, ascend to Blackwoods Wine & Cocktail Bar’s stylish sanctuary, where expert mixology and a curated wine list elevate the scene to a sophisticated crescendo. Together, these spots craft a dynamic journey of spirited sips and social adventures you won’t forget.
Launching the crawl with infectious energy, Naughty Nancy’s blends live music and bold flavors to ignite the night and set the party pulse racing.
The next stop is a short and lively stroll down Chapel Street, keeping the momentum buzzing as you head toward Better Days Cocktail Bar.
This playful hotspot injects fun and creativity with board games and quirky cocktails, offering a perfect social playground that elevates the night’s vibe.
The next stop is a quick, vibrant walk along Chapel Street, seamlessly guiding you to the sophisticated ambiance of Blackwoods Wine & Cocktail Bar.
Culminate the adventure in style at Blackwoods, where expert-crafted cocktails and a curated wine selection create an elegant yet spirited finale.
The next stop is the perfect finale, so no walk needed—just settle in and soak up the refined energy of the space.
This Windsor cocktail bar crawl is your passport to a night charged with rhythm, flavor, and unforgettable social sparks. Whether you’re toasting live beats, gaming with friends, or savoring top-tier cocktails, each venue builds on the last, crafting a night that thrills from first sip to last call. Ready to own the night? Grab your crew, follow the trail, and let Windsor’s Chapel Street nightlife write your next great story.
Crawl Map