đź“… Open Today: Crawl likely not fully open on Tuesdays
Experience the best of Windsor's nightlife with our cocktail bar crawl! Visit three top spots—Better Days Cocktail Bar, Blackwoods Wine & Cocktail Bar, and Three Monkeys—and enjoy a mix of creative cocktails, great atmospheres, and lively vibes. Perfect for anyone looking to explore quirky neighbourhood hangouts, sip expertly crafted drinks, and dance the night away with DJ parties on weekends. Grab your friends and let's make it a night to remember!
Last updated: June 2025
Kick off your night in Windsor with a cocktail bar hop that’s all about energy and excitement. This curated route along vibrant Chapel Street takes you from the fun, game-filled buzz of Better Days Cocktail Bar to the sophisticated yet easygoing atmosphere of Blackwoods Wine & Cocktail Bar. Finally, dive into the lively weekend vibes at Three Monkeys, where rhythmic beats and quirky style make the scene pop. Each stop hits its own unique groove — mixing creative drinks with fun social spots — for an evening of exploration, connections, and pure celebration.
Kick things off with a fun burst of energy at Better Days, where inventive cocktails come with a nostalgic lineup of video and board games. This welcoming spot is all about loosening up, starting conversations, and jumping into a social evening packed with laughs and lively vibes.
The next stop is a quick, energizing stroll down Chapel Street, keeping the good times rolling as you head to a sleek and stylish new spot.
Blackwoods amps up the hop with a sophisticated yet laid-back feel, where expertly crafted cocktails pair with a great wine selection in a space that’s perfect for chatting and enjoying every sip while deepening connections in style.
The next stop is just a short, easy walk along Chapel Street, sliding smoothly into a more intimate spot with rhythmic energy.
Wrap up the hop with a final energy boost at Three Monkeys, boasting quirky décor, excellent cocktails, and weekend DJ beats. This lively hangout is ideal for dancing, laughing, and celebrating the night with new friends in a spirited, adventurous close.
The next stop is a quick walk back to central Windsor or wherever your adventure leads, leaving you with that post-hop buzz.
This short Windsor cocktail bar hop captures the heart of Chapel Street’s buzzing nightlife — from playful starts to stylish middles and energetic finishes. Whether you’re a cocktail fan or just out for some social fun, this route delivers a night full of flavors, laughs, and memories. Ready to sip, savor, and mingle? Grab your crew, hit the street, and turn Windsor into your ultimate playground tonight.
Crawl Map