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 a snug, quirky neighbourhood hangout vibe. Whether you're into craft cocktails, lively DJ parties on weekends, or just a great night out with friends, this crawl has it all. Dive into Windsor's best spots for drinks, laughs, and unforgettable memories!
Last updated: July 2025
Embark on a spirited journey through Windsor’s Chapel Street with a cocktail bar crawl designed for those who crave excitement, creativity, and social connection. Begin your evening at Three Monkeys, where quirky charm meets pulsating weekend DJ sessions, setting the perfect energetic tone. Next, transition to Better Days Cocktail Bar, where playful nostalgia and inventive cocktails collide in an atmosphere charged with laughter and friendly competition. Finally, finish strong at Blackwoods Wine & Cocktail Bar, blending refined craftsmanship with a warm, inviting buzz that keeps the night alive. This crawl crafts a seamless arc of vibes—each stop amplifying the adventure and inviting you to savor Windsor’s dynamic nightlife one cocktail at a time.
Kick off the crawl inside Three Monkeys’ energetic yet intimate setting, where expertly mixed cocktails and weekend DJ beats ignite the night with quirky charm and lively social buzz.
The next stop is just a brief stroll away along Chapel Street, keeping the momentum flowing through Windsor’s vibrant heart.
Step into a lively playground of inventive drinks and nostalgic games, where Better Days Cocktail Bar fuels friendly competition and upbeat conversations, elevating the night’s energy with warmth and fun.
The next stop is a short, easy walk down Chapel Street, letting you soak in Windsor’s nightlife buzz between stops.
Conclude your crawl at Blackwoods, where refined cocktails and an inviting atmosphere balance sophistication with lively camaraderie, perfect for ending the night on a high note full of social energy.
The next stop is the close of the crawl, leaving you in the heart of Windsor’s vibrant nightlife to continue your adventure.
With every sip and step, this Windsor cocktail bar crawl delivers a dynamic blend of atmosphere, creativity, and social spark. Whether you’re chasing weekend beats, playful nostalgia, or refined vibes, these three spots craft a night to remember. Gather your crew, bring your adventurous spirit, and dive into Windsor’s cocktail scene where every bar is an invitation to shake up your night and toast to unforgettable memories.
Crawl Map