đź“… Open Today: Crawl likely open on Fridays
Explore Windsor's vibrant cocktail scene with our fun-filled pub crawl! Visit three awesome venues — Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar — each offering unique, quirky vibes and fantastic drinks. Whether you're into creative cocktails or relaxed neighbourhood hangouts, this crawl is perfect for a memorable night out with friends, topped off with DJ parties on weekends. Get ready for a friendly, lively evening in Windsor’s best bar spots!
Last updated: July 2025
Windsor’s Chapel Street bursts to life after dark, and this cocktail bar crawl captures its spirited pulse perfectly. Kick off your night at Three Monkeys, a charismatic spot where quirky décor meets infectious energy and weekend beats. From there, step into Better Days Cocktail Bar—where inventive drinks meet nostalgic gaming, sparking laughter and lively conversation. Finish strong at Blackwoods Wine & Cocktail Bar, where refined cocktails blend with an inviting atmosphere, making it the perfect finale for a night of adventure and social connection. This crawl isn’t just about drinks; it’s an escalating journey through Windsor’s dynamic cocktail culture that promises memorable moments and nonstop fun.
Three Monkeys sets the energetic tone for the night with its quirky charm and lively weekend DJ sessions. It’s the perfect launchpad to spark excitement and kickstart social connections with expertly mixed cocktails fueling the vibe.
The next stop is a quick, upbeat stroll down Chapel Street, keeping the energy alive as you head to a playful haven of games and inventive drinks.
Better Days injects a burst of social fun into the crawl with its mix of nostalgic video games and creative cocktails. It’s the ideal spot to deepen the night’s adventure with spirited competition and shared laughter.
The next stop is a short, vibrant walk along Chapel Street, setting the stage for a seamless transition into a more refined cocktail experience.
Blackwoods delivers a sophisticated yet lively finale, blending masterful cocktails and a welcoming atmosphere that invites you to unwind and celebrate the night’s shared adventures.
The next stop is the end of the crawl, perfectly positioned for easy departures or to continue exploring Windsor’s vibrant nightlife.
Ready to energize your night with a cocktail adventure that ramps up the fun at every stop? This Windsor crawl along Chapel Street is your ticket to dynamic vibes, delicious drinks, and unforgettable social moments. Gather your crew, pace yourself, and dive into a night where every sip and step brings new excitement. Cheers to chasing good times and great cocktails in Windsor!
Crawl Map