đź“… Open Today: Crawl likely open on Fridays
Explore Windsor's vibrant cocktail scene with our 3-venue crawl! Sip on creative drinks at Three Monkeys, enjoy stylish vibes at Better Days Cocktail Bar, and unwind at Blackwoods Wine & Cocktail Bar. Perfect for those who love a snug, quirky neighbourhood hangout with great cocktails and weekend DJ parties. Whether you're a local or just visiting, this crawl promises a fun-filled night with friends and fantastic drinks in a lively, friendly atmosphere.
Last updated: July 2025
Kick off your evening in Windsor with a cocktail bar crawl designed for thrill-seekers and social adventurers eager to explore Chapel Street’s dynamic nightlife. This handpicked trio of bars offers a seamless journey from infectious beats and quirky charm to playful nostalgia and finally to refined, vibrant sophistication. Each stop brings its own unique energy, keeping the momentum high and ensuring your night flows with excitement, laughter, and expertly mixed libations. Whether you’re rallying a crew or flying solo, this crawl turns the art of cocktail hopping into a lively urban adventure.
Launch your night at Three Monkeys, where intimate quarters meet pulsating weekend DJ sets. Its quirky vibe and curated cocktail menu energize the crowd, setting a vibrant tone that sparks conversation and dance alike.
The next stop is a short and inviting stroll along Chapel Street, keeping the buzz alive as you head to Better Days Cocktail Bar.
Better Days shifts the vibe into playful gear, mixing inventive cocktails with a dose of nostalgia through classic board and video games. This stop injects fun and friendly competition, amplifying the social energy as the night unfolds.
The next stop is a brisk walk down Chapel Street, letting the contagious energy carry you onward to Blackwoods Wine & Cocktail Bar.
Conclude your crawl at Blackwoods, where lively sophistication reigns. Expertly crafted cocktails and a curated wine list create a spirited yet polished atmosphere, perfect for capping off an adventurous night with vibrant conversations and stylish sips.
The next stop is the end of the crawl, leaving you perfectly poised to savor the afterglow of a night well spent in Windsor’s cocktail scene.
Ready to embrace Windsor’s cocktail culture in full throttle? This crawl is your passport to a night packed with thrilling energy, creative drinks, and social sparks. Lace up your walking shoes, gather your friends, and let Chapel Street’s lively venues guide you through an unforgettable adventure. Whether you’re a seasoned cocktail lover or chasing new nightlife thrills, Windsor delivers the perfect blend of excitement and flavor. Cheers to the night ahead!
Crawl Map