đź“… Open Today: Crawl likely open on Fridays
Join us for an unforgettable night out in Windsor with our cocktail bar crawl! Explore three vibrant venues—Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering unique, snug, and quirky neighbourhood hangouts. Whether you’re into expertly mixed cocktails or lively DJ parties on weekends, this crawl is perfect for a relaxed yet energetic evening. Get ready to sip, socialize, and dance your way through Windsor’s coolest cocktail spots!
Last updated: July 2025
Embark on a thrilling cocktail bar crawl through Windsor’s buzzing Chapel Street, where energetic crowds, creative mixology, and social adventure collide. Start your evening at Three Monkeys, where infectious energy and weekend DJ sessions set the perfect tone. Then, shift gears into playful mode at Better Days Cocktail Bar, blending nostalgic vibes with inventive cocktails and interactive games that spark laughter and connection. Finally, raise a glass at Blackwoods Wine & Cocktail Bar, where an elegant yet lively atmosphere welcomes groups and couples alike, rounding out your night with sophistication and spirited conversation. This crawl promises a dynamic flow of excitement, ensuring every stop elevates your night out.
Launch your night with Three Monkeys’ eclectic energy and expertly crafted cocktails, where intimate yet vibrant vibes and weekend DJ beats set an energizing tone for the adventure ahead.
The next stop is a quick and lively stroll down Chapel Street, keeping the momentum alive as you head to Better Days Cocktail Bar.
At Better Days, dive into a spirited mix of nostalgia and creativity with playful games and inventive cocktails, fueling fun social interactions and lifting the excitement to new heights.
The next stop is just a brief walk further along Chapel Street, allowing the buzz from Better Days to carry you seamlessly to Blackwoods Wine & Cocktail Bar.
Conclude your crawl at Blackwoods, where a lively yet polished atmosphere and sophisticated cocktails create the perfect setting for celebrating the night’s adventures with friends or dates.
The next stop is the end of the line—time to soak in the vibrant scene or plan your next Windsor night out from here.
Ready to own the night? This Windsor cocktail bar crawl delivers an electric mix of beats, bold drinks, and social sparks—perfect for adventurous souls eager to connect and celebrate. Lace up your walking shoes, gather your crew, and toast your way through Chapel Street’s top cocktail hotspots. Each venue promises a unique flavor of excitement, making this crawl your ultimate passport to Windsor’s nightlife thrills.
Crawl Map