đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant cocktail scene with our fun-filled bar crawl! Explore three unique venues — Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar — each offering their own quirky charm, snug atmospheres, and expertly crafted drinks. Perfect for a relaxed evening or lively weekend parties with DJs spinning tunes. Whether you're after creative cocktails or a cozy neighbourhood hangout, this crawl is your ticket to a memorable night out in Windsor!
Last updated: July 2025
Dive into Windsor’s buzzing cocktail culture with a bar crawl designed for those craving high-energy fun and expertly crafted drinks. Starting at Three Monkeys, you’ll soak in a lively yet intimate atmosphere where weekend DJ parties ignite the scene and every cocktail bursts with personality. Just a short stroll brings you to Better Days, a vibrant playground of nostalgic games and inventive concoctions that spark laughter and connection. The finale unfolds at Blackwoods Wine & Cocktail Bar, where elegant yet unpretentious vibes welcome groups and couples alike for a memorable nightcap. This crawl pulses with dynamic energy and social adventure—perfect for those ready to embrace Windsor’s spirited nightlife.
Launching your night at Three Monkeys sets an electric tone with its quirky, intimate space and weekend DJ sessions that spark lively conversations and dance-ready beats. It’s the perfect energetic launchpad to jumpstart the crawl’s social vibe.
The next stop is a quick, engaging stroll along Chapel Street, keeping the momentum alive as you head to Better Days.
Better Days amps up the adventure with its playful collection of board and video games paired with inventive cocktails. This stop invites you to dive into shared laughter and spirited competition, injecting a fresh burst of fun energy midway through the crawl.
The next stop is just a brief, lively walk further down Chapel Street, keeping the night’s pulse strong as you approach Blackwoods.
Closing the crawl at Blackwoods brings a sophisticated yet inviting atmosphere, where expertly crafted cocktails and a welcoming crowd offer the perfect setting to wind down without losing the night’s spirited energy. It’s an elegant finale that leaves the social buzz humming.
The next stop is the end of the crawl—time to savor your last sips and reflect on a night full of lively moments.
Ready to unlock Windsor’s dynamic cocktail scene? This crawl delivers a night packed with vibrant beats, playful interactions, and expertly crafted drinks. Whether you’re connecting with friends or meeting new faces, each stop builds on the last to keep energy high and spirits lifted. So lace up your walking shoes, bring your best cheers, and let Windsor’s cocktail adventure ignite your night.
Crawl Map