đź“… Open Today: Crawl likely open on Fridays
Ready for a night of sipping and socialising? Explore Windsor's quirky neighbourhood hangouts on this cocktail bar crawl! Visit three awesome spots—Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—and enjoy a mix of creative cocktails, snug atmospheres, and weekend DJ parties. Perfect for anyone looking to discover hidden gems and have a lively, memorable night out with friends!
Last updated: July 2025
Kick off an electrifying night in Windsor with a cocktail bar crawl designed for the adventurous spirit. This route threads through Chapel Street’s most dynamic watering holes, each offering a distinct slice of the city’s nightlife pulse. Begin your journey enveloped in the quirky charm and rhythmic energy of Three Monkeys, where expertly crafted cocktails meet weekend DJ flair. Next, shift gears into a playful social playground at Better Days Cocktail Bar, a spot blending nostalgic games with innovative drinks—perfect for laughter-fueled catch-ups. Finally, round out your expedition at Blackwoods Wine & Cocktail Bar, an inviting haven where refined cocktails and a curated wine list elevate the evening’s momentum. Together, these stops create a thrilling crescendo of flavors, vibes, and connections that define Windsor’s cocktail culture.
Launching the crawl with its quirky, upbeat energy and weekend DJ parties, Three Monkeys sets a vibrant tone with lively cocktails and an intimate yet spirited atmosphere.
The next stop is a brief stroll down Chapel Street, a convenient and lively walk that keeps the night’s momentum flowing toward your next playful destination.
Better Days shifts the vibe into a fun, social playground where inventive cocktails meet nostalgic games, sparking joyful interactions and lighthearted competition among friends.
The next stop is a short and easy walk along Chapel Street, sustaining the energy with a seamless transition into a more refined cocktail experience.
Concluding the crawl, Blackwoods wraps the night in sophisticated warmth with its expertly crafted cocktails and curated wine selection, perfect for deepening conversations and celebrating the night.
The next stop is the final destination, so you can settle in and savor the bar’s inviting ambiance without needing to move on.
This Windsor Cocktail Bar Crawl delivers a night packed with energy, creativity, and connection. Whether you’re a cocktail connoisseur or simply chasing good times with great company, this journey through Chapel Street’s top bars promises unforgettable memories. Ready to mix, mingle, and explore? Grab your crew and dive into Windsor’s spirited cocktail scene tonight!
Crawl Map