đź“… Open Today: Crawl likely open on Fridays
Join us on a fun-filled Windsor cocktail crawl through three vibrant venues: Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. This quirky neighborhood hangout offers the best beer, cocktails, and lively DJ parties on weekends. Perfect for a night out with friends, explore cozy snug spots and unique atmospheres that make Windsor’s nightlife unforgettable. Cheers to good times and great drinks!
Last updated: July 2025
Kick off your night in Windsor with a cocktail bar crawl designed to ignite your sense of adventure and social spirit. Beginning at Three Monkeys, you’ll be welcomed by an atmosphere alive with upbeat tunes and expertly mixed drinks, setting the perfect tone for the evening. From there, dive into Better Days, where playful nostalgia meets creative cocktails — think classic games, vibrant projections, and a contagious buzz that invites shared laughs and new connections. The finale awaits at Blackwoods Wine & Cocktail Bar, where sophistication blends with lively energy, offering a curated wine list and cocktails crafted to perfection. This crawl flows seamlessly from spirited beats to interactive fun and then to refined conviviality, ensuring every moment pulses with excitement and fresh experiences.
Launching the crawl with vibrant energy, Three Monkeys sets the stage with its dynamic cocktail menu and weekend DJ sessions that get the night moving. Its quirky, cozy vibe invites early mingling and lively conversations, sparking the social adventure ahead.
The next stop is a quick stroll down Chapel Street, keeping the energy high as you head toward a spot brimming with playful nostalgia and interactive fun.
Better Days shifts gears into a lively playground of inventive cocktails, classic video games, and immersive projections. This stop amplifies the night’s social pulse, encouraging shared laughter and spontaneous competition in an atmosphere that’s both vibrant and welcoming.
The next stop is a brief walk along Chapel Street, leading you to a stylish venue where refined flavors and spirited conversations await to close out the crawl.
Concluding the adventure, Blackwoods offers a sleek yet approachable setting where expertly crafted cocktails and select wines fuel engaging conversations and celebration. It’s the perfect spot to toast the night’s memories and newfound connections with elegance and buzz.
The next stop is the end of the crawl, leaving you perfectly positioned to continue your night or savor the afterglow nearby.
Ready to turn your next night out into an unforgettable escapade? This Windsor cocktail bar crawl invites you to explore Chapel Street’s pulse through three distinct yet seamlessly connected venues. Whether you’re hunting for inventive cocktails, social buzz, or a lively scene to share with friends, this adventure delivers every step of the way. Grab your crew, map your route, and let the night unfold with spirited drinks, dynamic vibes, and endless fun.
Crawl Map