đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant cocktail scene with our exclusive 3-venue crawl! Start at Naughty Nancy's, then sip your way through Better Days Cocktail Bar and Blackwoods Wine & Cocktail Bar. Perfect for food lovers and cocktail enthusiasts alike, this pub crawl combines great drinks, lively atmospheres, and unforgettable memories. Whether you're celebrating or just looking for a fun night out, this route is your ticket to Windsor’s best cocktail spots!
Last updated: July 2025
Get ready to ignite your night in Windsor with a cocktail bar crawl that pulses with energy and social adventure. This curated route starts at Naughty Nancy’s, where bold flavors and live music set an electric tone. Next, step into Better Days, a playful hotspot where inventive cocktails meet nostalgic games, sparking laughter and connection. Finally, settle into the elegant yet approachable atmosphere of Blackwoods Wine & Cocktail Bar, where expert mixology and a carefully selected wine list elevate the evening. Each stop builds on the last, creating a dynamic flow from spirited beginnings to a sophisticated finale — perfect for anyone craving an unforgettable night out in Windsor’s buzzing Chapel Street corridor.
As the energetic launchpad for the crawl, Naughty Nancy’s pairs vibrant live music and hearty, flavor-packed fare with craft cocktails, instantly immersing you in Windsor’s lively nightlife spirit.
The next stop is just a short and engaging stroll along Chapel Street, keeping the night’s momentum alive while transitioning to a more playful and intimate vibe.
Better Days shifts the energy into a fun, social playground with inventive cocktails, cozy seating, and interactive games — a lively space that invites camaraderie and laughter to deepen the night’s adventure.
The next stop is a brief and easy walk down Chapel Street, giving just enough time to anticipate the final spot’s elevated cocktail mastery.
Blackwoods closes the crawl with sophisticated charm and expertly crafted drinks, providing a vibrant yet polished setting that rounds out the evening with style and a welcoming buzz.
The crawl concludes here; no further walking is needed, allowing you to savor your final cocktails and reflect on an exhilarating night.
This Windsor cocktail bar crawl delivers a seamless journey through vibrant energy, playful social moments, and refined mixology mastery. Whether you’re a local or visiting, each stop promises memorable flavors, dynamic atmospheres, and spirited connections. So gather your crew, hit the pavement, and let Windsor’s Chapel Street reveal its lively cocktail secrets — your next great night out awaits!
Crawl Map