đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant nightlife on this lively cocktail crawl through four quirky venues: Three Monkeys, Better Days Cocktail Bar, Blackwoods Wine & Cocktail Bar, and Bar Blanco. Perfect for those who love a snug, neighborhood hangout with great drinks, cool vibes, and DJ parties on weekends. Whether you're after craft cocktails or a relaxed wine night, this crawl promises a fun, memorable evening in Windsor’s best spots. Grab your friends and get ready for a night out you won't forget!
Last updated: July 2025
Kick off an electrifying night on Windsor’s iconic Chapel Street, where every stop amps up the excitement and social energy. This crawl launches in the quirky, intimate atmosphere of Three Monkeys, where expertly crafted cocktails meet vibrant weekend beats, setting the tone for a night full of connection and fun. Just a short stroll takes you to Better Days Cocktail Bar—a playful oasis combining nostalgia with inventive drinks and a lively social scene fueled by board games and video classics. The momentum continues with Blackwoods Wine & Cocktail Bar, where polished yet approachable vibes invite you to savor refined cocktails and a curated wine list amidst engaging company. Finally, the crawl crescendos at Bar Blanco, a glowing hotspot bursting with fresh flavors, spirited margaritas, and an infectious buzz that will keep your night alive well past last call. This bar journey masterfully balances varied atmospheres, delivering a seamless progression from vibrant intimacy to bold celebration, perfect for adventurers craving a night full of surprises and social thrills.
Launch your night at Three Monkeys, where quirky charm meets energetic weekend DJs and expertly mixed cocktails, creating a dynamic yet intimate setting to spark lively conversations and set the night’s adventurous tone.
The next stop is a brief, inviting walk down Chapel Street that keeps the energy flowing toward the playful vibe of Better Days Cocktail Bar.
Step into a world of nostalgic fun and inventive cocktails at Better Days, where vibrant social energy bubbles over with board games and video classics, perfect for connecting and laughing with friends before the evening deepens.
The next stop is a short, energizing stroll that leads you to the refined yet lively ambiance of Blackwoods Wine & Cocktail Bar.
Elevate your night at Blackwoods, where sophisticated cocktails and a curated wine list blend with a warm, vibrant atmosphere—offering a polished social hub that bridges playful beginnings with the night’s spirited climax.
The next stop is a lively, upbeat walk that brings you to the glowing energy and bold flavors of Bar Blanco.
Cap off your adventure at Bar Blanco, where glowing amber lights and signature margaritas fuel a buzzing scene of warmth and celebration, delivering an unforgettable finale packed with flavor and vibrant social energy.
The next stop is the end of the crawl, leaving you energized and ready to continue the night wherever your adventurous spirit leads.
From the quirky beats of Three Monkeys to the fiery margaritas at Bar Blanco, this Windsor bar crawl offers a seamless journey through Chapel Street’s most electrifying spots. Whether you’re seeking crafted cocktails, spirited games, or a buzzing crowd, each venue introduces a fresh layer of excitement that keeps the night alive and your social circle expanding. Ready to dive into Windsor’s nightlife adventure? Grab your crew, follow the flow, and let the night unfold with endless fun and unforgettable moments.
Crawl Map