đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant cocktail scene with our fun-filled crawl through three top venues: Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. This friendly, quirky neighbourhood hangout offers the perfect mix of snug atmospheres, creative cocktails, and lively DJ parties on weekends. Whether you're after unique drinks or a lively night out, this crawl is your ticket to Windsor’s coolest spots for a memorable evening with friends.
Last updated: July 2025
Kick off an unforgettable night on Windsor’s bustling Chapel Street, where this cocktail bar crawl ignites your evening with bold flavors, pulsating energy, and spirited social adventures. Begin in the infectious buzz of Three Monkeys, where quirky charm and weekend DJ beats set a dynamic tone. Transition seamlessly into Better Days Cocktail Bar’s playful playground of retro games and imaginative cocktails, sparking laughter and friendly competition. Finally, settle into the sophisticated yet inviting atmosphere of Blackwoods Wine & Cocktail Bar, the perfect finale for savoring expertly crafted drinks and vibrant conversations. This curated route delivers a thrilling crescendo of tastes and vibes, ensuring every stop elevates the night’s momentum and social spirit.
Launch your night at Three Monkeys, where an energetic yet intimate setting combines expertly mixed cocktails with weekend DJ sessions, creating the perfect high-voltage kickoff to the crawl.
The next stop is just a short, lively stroll down Chapel Street, keeping the vibrant energy flowing as you head to Better Days Cocktail Bar.
Amp up the fun with Better Days Cocktail Bar’s nostalgic vibe, where inventive cocktails meet playful board and video games, transforming the night into an interactive celebration of flavor and camaraderie.
The next stop is a quick and energetic walk along Chapel Street, perfect for keeping the momentum alive as you make your way to Blackwoods Wine & Cocktail Bar.
Cap off the crawl at Blackwoods, where a lively yet polished atmosphere hosts masterfully crafted cocktails and curated wines, setting the stage for vibrant conversations and a memorable finale.
The crawl concludes here, so no more walking—just settle in for the night’s exhilarating finish.
This Windsor cocktail bar crawl delivers a charged sequence of experiences, blending infectious energy, playful moments, and refined hospitality. Whether you're out with friends or meeting new ones, each stop is designed to elevate your night, leaving you buzzing with stories and inspired for your next adventure. Ready to take on Chapel Street? Gather your crew, pace yourself, and savor every exhilarating sip along the way.
Crawl Map