đź“… Open Today: Crawl likely open on Fridays
Explore 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. Discover snug, quirky neighbourhood hangouts perfect for sipping cocktails or grabbing a beer, with lively DJ parties on weekends. Whether you're into creative drinks or just looking for a relaxed spot with great vibes, this crawl promises a memorable night in Windsor’s coolest bars.
Last updated: July 2025
Dive headfirst into Windsor’s buzzing nightlife with this carefully curated cocktail bar crawl along Chapel Street. Kicking off with the spirited energy of Three Monkeys, where expertly crafted drinks meet infectious DJ sets, this crawl invites you to unleash your adventurous side. Next, amp up the fun with Better Days Cocktail Bar’s playful mix of retro games and inventive cocktails—perfect for sparking lively conversations and friendly competition. Finally, wrap up your night at Blackwoods Wine & Cocktail Bar, where elegance meets vivacity in a welcoming space designed for meaningful connections and memorable toasts. This crawl is your passport to a night packed with excitement, social buzz, and unforgettable flavors.
Launch your night in style at Three Monkeys, where a lively ambiance and upbeat DJ sets create the perfect energetic backdrop for your first cocktail. Its quirky charm and warm service set the tone for a dynamic evening ahead.
The next stop is a quick and inviting stroll down Chapel Street, keeping the vibrant energy flowing as you head to Better Days Cocktail Bar.
Step into a world of playful competition and creative cocktails at Better Days Cocktail Bar, where retro video games and board games blend with a lively atmosphere, fueling fun interactions and fueling your social adventure.
The next stop is a brief walk along the bustling Chapel Street, transitioning seamlessly to the sophisticated vibe of Blackwoods Wine & Cocktail Bar.
Conclude your crawl with a flourish at Blackwoods Wine & Cocktail Bar, where an elegant yet spirited ambiance welcomes you to savor refined cocktails and celebrate the night’s vibrant journey with friends old and new.
The next stop is the perfect moment to reflect on the night’s highlights — Blackwoods is your final destination on this spirited Windsor crawl.
Ready to ignite your night in Windsor? This cocktail bar crawl delivers a nonstop wave of energy, unique vibes, and social thrills from start to finish. Whether you’re a local or visiting adventurer, these Chapel Street gems promise unforgettable moments and sensational sips. Grab your crew, map your route, and let the Windsor Cocktail Bar Adventure lead you through a night charged with flavor, fun, and friendship. Cheers to your next epic night out!
Crawl Map