đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's lively cocktail scene with our fun-filled bar crawl! Explore three fantastic venues—Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering unique drinks and great vibes. Perfect for food lovers and cocktail enthusiasts alike, this crawl is your chance to enjoy expertly crafted drinks, vibrant atmospheres, and a memorable night out. Grab your friends and let’s toast to good times!
Last updated: July 2025
Kick off your Windsor night on Chapel Street where every stop amps up the excitement. This cocktail crawl is crafted for those hungry for more than just drinks — it’s a social adventure packed with live music, playful competition, and expert mixology. Begin at Naughty Nancy’s, where the pulse of live bands and irresistible bites set the tone for a night of fun. Then, shift gears into a playful lounge atmosphere at Better Days, where classic video games and innovative cocktails spark laughter and friendly challenges. Finally, wind down with style at Blackwoods, a chic spot blending a curated wine list and cocktails in an atmosphere that invites connection and celebration. This crawl is your passport to Windsor’s dynamic blend of energy, creativity, and spirited socializing.
Launching your crawl here means diving straight into Windsor’s energetic heartbeat—live music, hearty eats, and craft cocktails fuel the lively, buzzing atmosphere that kickstarts the night with an unbeatable vibe.
The next stop is a short, vibrant stroll down Chapel Street, keeping the energy flowing as you move from live music to playful cocktail fun.
Better Days keeps the momentum alive with its inviting, game-filled lounge where inventive cocktails and a nostalgic vibe spark laughter, making it the perfect social playground after the high-energy start.
The next stop is just a quick walk along Chapel Street, transitioning smoothly from playful fun to refined cocktail sophistication.
Closing out the crawl, Blackwoods offers a polished yet welcoming setting ideal for savoring expertly crafted cocktails and wines, rounding off the night with stylish comfort and lively conversations.
The next stop concludes the crawl here, leaving you perfectly positioned to continue your Windsor night or reflect on a night well spent.
This Windsor cocktail bar crawl is your gateway to a night packed with vibrant energy, inventive drinks, and memorable social moments. Whether you’re a local or visiting, hit these three hotspots to experience Chapel Street’s electrifying nightlife from the first sip to the last call. Ready to sip, play, and savor? Grab your crew and let Windsor’s cocktail scene sweep you off your feet.
Crawl Map