đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s coolest cocktail bars on this lively crawl! Visit three fantastic spots—Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each with their own unique vibe. Whether you’re into snug neighborhoods, quirky hangouts, or weekend DJ parties, this crawl has it all. Perfect for a fun night out with friends, tasting creative cocktails, and dancing the night away in Windsor’s vibrant bar scene.
Last updated: July 2025
Dive headfirst into Windsor’s buzzing Chapel Street with a cocktail crawl designed for those who crave a night packed with energy, social sparks, and inventive libations. This curated trio of bars crafts a seamless journey from the intimate, quirky charm of Three Monkeys, where weekend rhythms ignite the night, through the playful, game-filled atmosphere of Better Days Cocktail Bar, and culminating in the polished yet vibrant scene at Blackwoods Wine & Cocktail Bar. Each stop brings a fresh burst of character and excitement, ensuring this crawl builds momentum with every sip and step.
Kicking off the crawl with a punch, Three Monkeys sets the tone with its quirky décor and a lively cocktail menu that invites connection and celebration. The weekend DJ sessions add a soundtrack of energy that sparks conversations and ignites the night.
The next stop is a short, upbeat stroll along Chapel Street, keeping the buzz alive as you head toward your next playful destination.
Better Days amps up the fun with its eclectic mix of classic and modern video games paired with inventive cocktails, creating a social playground where competitive spirits and laughter flow freely.
The next stop is just a quick, energetic walk down Chapel Street, perfect to stretch your legs and keep the night’s momentum building.
Rounding out the adventure, Blackwoods offers a refined yet vibrant atmosphere, where expertly crafted cocktails and a curated wine list provide the perfect backdrop for lively conversations and celebratory toasts.
The crawl concludes here, nestled conveniently on Chapel Street, leaving you perfectly poised to continue your night or savor the memories made.
Embark on this Windsor cocktail bar crawl to unlock the spirited heart of Chapel Street. From quirky beats to playful games and elegant sips, this night promises endless adventure and unforgettable moments. Gather your crew, pace your pours, and let the vibrant energy of Windsor’s best cocktail spots carry you through a night of social thrill and spirited fun.
Crawl Map