đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant cocktail scene with our exclusive bar crawl! Explore three fantastic venues—Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering unique, cozy atmospheres perfect for a relaxed evening or weekend DJ parties. Whether you're into creative cocktails or snug neighborhood hangouts, this crawl is your ticket to a memorable night out in Windsor. Grab your friends and get ready for a fun, lively evening!
Last updated: July 2025
Windsor’s Chapel Street pulses with excitement, and this cocktail bar crawl taps right into its adventurous spirit. Launch your night at Three Monkeys, where quirky charm meets DJ-fueled energy, setting the stage with expertly mixed cocktails and an infectious vibe. Next, shift gears to Better Days Cocktail Bar, a playground of innovative drinks paired with nostalgic board games and iconic video game projections that spark laughter and lively competition. Finally, round out your evening at Blackwoods Wine & Cocktail Bar, where polished mixology meets a welcoming atmosphere, perfect for savoring refined cocktails and raising a toast to a night well spent. This crawl is designed to keep the momentum flowing, turning each stop into a distinctive chapter of your social adventure.
Kick off the crawl at Three Monkeys, a vibrant hub where expertly crafted cocktails meet weekend DJ energy, igniting the night with playful vibes and social buzz.
The next stop is just a short, lively stroll along Chapel Street, keeping the energy high as you move towards more interactive fun.
Step into Better Days for a dynamic shift—a spirited scene where inventive cocktails blend with nostalgic games, sparking friendly competition and infectious laughter.
The next stop is a quick walk down Chapel Street, maintaining the momentum as you head to the evening’s elegant finale.
Conclude your adventure at Blackwoods, where sophisticated cocktails and a refined yet inviting atmosphere offer the perfect setting to celebrate the night’s journey.
The crawl ends here, letting you settle into the night with ease or explore Windsor’s nightlife further from this stylish hotspot.
This Windsor cocktail bar crawl delivers a curated sequence of lively, engaging experiences that elevate your night from start to finish. Whether you’re savoring the infectious energy at Three Monkeys, sharing laughs over games at Better Days, or toasting in style at Blackwoods, each stop builds on the last to craft an unforgettable social adventure. Ready to raise your glass and dive into Windsor’s spirited nightlife? Gather your crew and let this crawl guide you through the best cocktails and vibes Chapel Street has to offer.
Crawl Map