đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant cocktail scene with our exciting pub crawl! Visit 3 fantastic venues – Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar – each offering unique drinks, lively atmospheres, and tasty bites. Perfect for anyone who loves food-centric pub experiences, this crawl is your ticket to a memorable night of cocktails, conversation, and good times. Grab your friends and get ready to explore Windsor’s best bars!
Last updated: July 2025
Get ready to ignite your night with the Windsor Cocktail Bar Crawl—a high-energy journey through Chapel Street’s most exciting drinking destinations. This crawl starts strong at Naughty Nancy’s, where live music and hearty bites set the stage for an evening charged with buzz and flavor. Next, shift gears into a playful realm at Better Days Cocktail Bar, where retro games and inventive cocktails invite you to let loose and connect. Finally, settle into the stylish comfort of Blackwoods Wine & Cocktail Bar, where expert mixology meets an effortlessly inviting atmosphere. Each stop ramps up the fun and crafts a seamless progression from lively beats to charismatic charm, promising a dynamic night packed with memorable sips, smiles, and social adventures.
Launching the crawl with a buzz, Naughty Nancy’s pulses with live music and a food-focused menu that fuels the night. Its energetic vibe creates the perfect kickoff point, where craft cocktails meet a crowd ready to dive into Windsor’s nightlife.
The next stop is a quick and lively stroll down Chapel Street, keeping the energy flowing as you head toward a playful cocktail haven.
Better Days amps up the fun with its nostalgic gaming corners and inventive drinks, inviting you to mix friendly competition with expert-crafted cocktails for a uniquely vibrant stop.
The next stop is just a brisk walk away, allowing you to carry the spirited buzz forward into a more refined setting.
Closing the crawl, Blackwoods delivers polished sophistication without losing warmth. Its expertly crafted cocktails and curated wine list provide a stylish backdrop for wrapping up your adventurous night on a high note.
The crawl concludes here, so no further walking is needed—time to savor the last sips and memories.
This Windsor Cocktail Bar Crawl offers more than just drinks—it’s a curated adventure through Chapel Street’s lively heartbeat. Whether you’re chasing live tunes, game nights, or expertly shaken cocktails, each stop builds on the last to keep your night energized and unforgettable. Ready to raise your glass and explore Windsor’s spirited side? Gather your crew and dive into this cocktail-fueled journey that promises nonstop fun and social thrills.
Crawl Map