đź“… Open Today: Crawl likely open on Fridays
Discover 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, tasty bites, and lively atmospheres across some of Windsor’s top bars, pubs, and event venues. Grab your friends and make it a night to remember!
Last updated: July 2025
Kick off your night in Windsor with an electrifying cocktail bar crawl that pulses with energy, fun, and social adventure. Begin at Naughty Nancy’s, where live beats and bold flavors set a spirited tone, fueling the excitement. Transition to Better Days Cocktail Bar, a playful hotspot where nostalgia meets creativity, inviting you to unwind with cocktails and classic games that spark laughter and connection. Cap the night at Blackwoods Wine & Cocktail Bar, where masterfully crafted drinks meet a warm, inviting atmosphere—perfect for savoring the last moments of your vibrant journey. This crawl is designed to elevate your evening with seamless vibe shifts, engaging experiences, and unforgettable sips.
Starting the crawl at Naughty Nancy’s sets an exhilarating pace with its lively live music and robust, food-centric menu. The bustling energy and friendly crowds create the perfect launchpad for an adventurous night on the town.
The next stop is a short, invigorating stroll down Chapel Street, keeping the night’s momentum alive as you head toward Better Days Cocktail Bar.
Better Days infuses the crawl with playful charm and inventive cocktails. Its cozy, game-filled setting invites you to engage, laugh, and bond, offering a lively contrast to the opening stop’s spirited pub scene.
The next stop is a quick, scenic walk along Chapel Street, giving you just enough time to anticipate the refined yet vibrant atmosphere awaiting at Blackwoods.
Concluding the crawl at Blackwoods brings a sophisticated crescendo to the night. With expertly crafted cocktails and a welcoming ambiance, it’s the ideal spot to savor the final moments of your high-energy Windsor adventure.
The crawl ends here, allowing you to settle in and soak up the vibrant Chapel Street nightlife or plan your next exciting move.
Ready to ignite your night with unforgettable flavors, buzzing energy, and engaging company? This Windsor cocktail bar crawl delivers a seamless, pulse-raising journey through Chapel Street’s best spots. Whether you’re chasing live music, playful vibes, or crafted elegance, every stop promises to amplify your night. Lace up your walking shoes, rally your crew, and dive headfirst into Windsor’s cocktail scene—where every sip is a new adventure waiting to unfold.
Crawl Map