đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s best cocktail bars on this lively crawl! Visit five fantastic venues including Naughty Nancy's with its ship-themed vibe, Better Days Cocktail Bar’s tropical tiki mugs, Blackwoods Wine & Cocktail Bar’s cozy ambiance, Holy Grail’s contemporary lounge, and Jungle Boy’s plant-filled hangout. Perfect for cocktail lovers and night owls, this crawl offers a mix of rum, tiki, and innovative drinks in diverse settings. Grab your friends and get ready for an unforgettable night out!
Last updated: July 2025
Dive into Windsor’s buzzing Chapel Street on this cocktail bar crawl built for thrill-seekers and social adventurers. Kick off your night at Naughty Nancy’s, where lively beats and hearty bites set an energetic tone. From there, shift gears to Better Days, a playful spot filled with board games and nostalgic charm that sparks laughter and connection. The journey continues at Blackwoods, where refined cocktails meet approachable elegance, perfect for deepening conversations. Holy Grail then invites you aboard its ship-themed sanctuary, balancing cozy vibes with crafted rum concoctions. Finally, unleash your wild side at Jungle Boy, a tropical oasis where exotic cocktails and lush greenery deliver an unforgettable finale. Each stop builds on the last, creating a dynamic flow that keeps energy high and spirits lifted throughout the night.
Naughty Nancy’s kicks off the crawl with its infectious energy, combining lively live music and bold craft cocktails that instantly immerse you in Windsor’s vibrant nightlife.
The next stop is just a short, lively stroll along Chapel Street, keeping the momentum flowing as you head toward Better Days.
Better Days injects playful energy into the crawl with cozy seating, nostalgic video games, and inventive cocktails—perfect for sparking shared laughs and good vibes with friends.
The next stop is a quick and easy walk down Chapel Street, letting you soak up the buzzing atmosphere as you make your way to Blackwoods.
Blackwoods elevates the experience with polished, expertly crafted cocktails and a welcoming ambiance that’s ideal for both intimate chats and lively group celebrations.
The next stop is a brief stroll that carries you seamlessly into the cozy embrace of Holy Grail’s ship-inspired setting.
Holy Grail offers a unique nautical retreat, where plush seating and top-notch rum cocktails invite you to relax and reconnect before the night’s grand finale.
The next stop is a short, easy walk along Chapel Street, priming you for the tropical escape awaiting at Jungle Boy.
Jungle Boy closes the crawl with a burst of tropical flair—lush plants, exotic tiki cocktails, and a vibrant, spirited atmosphere that leave you buzzing with excitement.
This is the final stop on the crawl, perfectly placed to savor Windsor’s vibrant nightlife before you decide where the night takes you next.
Ready to conquer Windsor’s Chapel Street cocktail scene? This crawl is your passport to an electrifying night filled with inventive drinks, engaging atmospheres, and new friendships around every corner. Whether you’re celebrating a special occasion or just craving a night of adventure, these five hotspots deliver unforgettable moments and taste sensations. Grab your crew, charge your phone, and let the Windsor Cocktail Bar Crawl ignite your night with endless fun and flavor.
Crawl Map