đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s coolest cocktail bars on this lively crawl through three awesome venues: Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Perfect for anyone looking to enjoy a snug, quirky neighbourhood hangout with creative drinks and weekend DJ parties. Whether you’re into craft cocktails or relaxing with friends, this crawl promises a fun-filled night in Windsor’s vibrant bar scene. Cheers to good times!
Last updated: July 2025
Get ready to ignite your night with an electrifying cocktail bar crawl along Windsor’s iconic Chapel Street. This trio of bars crafts a magnetic journey — from the pulsing weekend DJ energy of Three Monkeys to the nostalgic fun and buzzy atmosphere of Better Days Cocktail Bar, culminating in the polished yet warmly inviting setting of Blackwoods Wine & Cocktail Bar. Each stop brings a new dimension of excitement and social adventure, ensuring your night flows seamlessly from dynamic beats to playful camaraderie and finally, elegant sips. Whether you’re rallying a group or seeking an unforgettable solo outing, this crawl promises a lively, cocktail-fueled exploration of Windsor’s spirited nightlife.
Kick off your crawl at Three Monkeys, where infectious energy and expertly crafted cocktails set a vibrant tone. This spot’s lively vibe, boosted by weekend DJ sessions, immediately immerses you in Windsor’s energetic nightlife, sparking connections and fueling the party spirit.
The next stop is a short, lively stroll along Chapel Street, keeping the buzz alive as you head toward a more playful and intimate cocktail experience.
At Better Days, the energy pivots to a joyful blend of nostalgia and creativity. Here, inventive cocktails meet arcade games and iconic projections, inviting you to unwind with friends while keeping the night’s momentum playful and vibrant.
The next stop is a brief, easy walk down Chapel Street, transitioning the vibe toward a refined yet approachable cocktail lounge.
Conclude your crawl at Blackwoods, where sophisticated cocktails and a curated wine list create an elegant finale. The atmosphere strikes a perfect balance — lively enough to keep the energy flowing but intimate enough to savor each crafted drink and meaningful conversation.
The next stop is the perfect wrap-up point; no more walking needed as you settle in to enjoy the night’s climax.
This Windsor cocktail bar crawl invites you to dive headfirst into a night of bold flavors, dynamic atmospheres, and social adventure. From the thumping beats and vibrant crowd at Three Monkeys to the playful charm of Better Days and the refined sophistication of Blackwoods, each stop builds on the last to deliver an unforgettable night out. Gather your crew or venture solo — either way, Windsor’s Chapel Street cocktail scene awaits with open arms and expertly poured drinks. Ready to taste the excitement? The night is yours.
Crawl Map