đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant cocktail scene on this exciting 3-venue crawl! Explore cozy, quirky neighbourhood hangouts like Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Perfect for those who love unique atmospheres, craft cocktails, and weekend DJ parties. Whether you're into laid-back vibes or lively nights, this crawl offers a fun-filled evening with the best bars Windsor has to offer. Grab your friends and get ready for a memorable night!
Last updated: July 2025
Windsor’s Chapel Street pulses with cocktail culture, and this curated crawl captures its electric spirit perfectly. Start your evening at Three Monkeys, where quirky charm meets weekend DJ energy, setting a playful tone for the night. Next, shift gears at Better Days Cocktail Bar, where nostalgia-infused games and inventive drinks invite you to laugh, compete, and connect. Finish strong at Blackwoods Wine & Cocktail Bar, a refined yet welcoming spot where expert mixology and a curated wine list craft the perfect finale. This crawl is a lively adventure that blends eclectic atmospheres with social buzz, promising a night packed with dynamic vibes and memorable moments.
Launch your crawl amid Three Monkeys’ energetic yet intimate setting, where quirky decor and weekend DJs inject a vibrant pulse, making it the ideal primer for a night of crafted cocktails and lively socializing.
The next stop is a short, inviting stroll along Chapel Street, keeping the energy flowing as you head deeper into Windsor’s cocktail scene.
Amp up the adventure at Better Days, where nostalgic arcade games and creative cocktails create a spirited playground for friends and flirtations, perfectly balancing fun competition with vibrant conviviality.
The next stop is just a few lively minutes’ walk down Chapel Street, allowing you to savor Windsor’s animated nightlife vibe as you approach your final destination.
Conclude your crawl at Blackwoods, where polished mixology and a curated wine selection invite you to unwind in a warm, dynamic atmosphere—perfect for raising a final toast to a night of spirited discovery.
The next stop is the end of the line for this crawl, leaving you perfectly poised to either continue your night or savor the memories of a well-crafted adventure.
This Windsor cocktail bar crawl is more than a night out—it’s an energetic journey through the vibrant heart of Chapel Street’s nightlife. From the infectious beats of Three Monkeys to the playful aura of Better Days and the elegant finish at Blackwoods, each stop builds on the last to create an unforgettable social adventure. Raise your glass to discovery, connection, and the endless fun of Windsor after dark. Ready to dive in? Your spirited exploration awaits.
Crawl Map