đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant cocktail scene on this fun-filled pub crawl! Visit five fantastic venues including Naughty Nancy's, Better Days Cocktail Bar, Blackwoods Wine & Cocktail Bar, Holy Grail, and Jungle Boy. Whether you’re into rum, tiki mugs, or cozy ship-themed spots, this crawl offers a mix of food-centric pubs, trendy bars, and lively nightclubs. Perfect for a night out with friends, savor delicious drinks, and soak up the lively Windsor atmosphere!
Last updated: July 2025
Get ready to ignite your night with the Windsor Cocktail Bar Crawl, a carefully curated journey through the beating heart of Chapel Street’s cocktail scene. This adventure kicks off with the dynamic energy of Naughty Nancy’s, where live music and bold flavors set an infectious tone. From there, shift gears at Better Days Cocktail Bar with its playful mix of classic gaming and creative cocktails, perfect for sparking laughter and connection. Elevate your palate next at Blackwoods Wine & Cocktail Bar, where expert craftsmanship meets a welcoming atmosphere, balancing refinement with fun. Dive deeper into character at Holy Grail, a ship-inspired bar where exquisite rums and handcrafted drinks invite you to linger in plush comfort. The crawl sails to its grand finale at Jungle Boy, an urban tropical oasis blending exotic botanicals, innovative tiki cocktails, and a lush ambiance that leaves you buzzing. Every stop builds on the last, weaving an exhilarating night of taste, social discovery, and spirited celebration.
Kick off the crawl with Naughty Nancy’s electrifying energy where live music pulses alongside craft cocktails and bold, food-driven flavors that fuel your night ahead.
The next stop is a short, easy stroll along Chapel Street, keeping the momentum alive as you move from the buzzing pub to a cozy cocktail lounge.
Step into a lively, welcoming atmosphere at Better Days, where inventive drinks meet playful vibes—perfect for sparking fun and friendly competition over board games.
The next stop is a quick, vibrant walk further down Chapel Street, transitioning from playful energy to sophisticated sips.
Elevate your evening at Blackwoods, where expertly crafted cocktails and a curated wine list create an elegant yet approachable scene, perfect for mingling and savoring every sip.
The next stop is a brief, engaging walk that shifts the vibe towards a cozy, thematic experience with a twist of adventure.
Immerse yourself in Holy Grail’s ship-inspired charm, where rich rums and hand-crafted cocktails invite intimate conversations amid plush, vintage surroundings.
The next stop is just a short, atmospheric walk along Chapel Street, leading to a vibrant tropical finale.
Conclude your crawl in lush style at Jungle Boy, a tropical hideaway serving daring tiki cocktails in a plant-filled lounge that pulses with exotic energy and spirited fun.
The crawl wraps up here, giving you the perfect spot to linger, celebrate, or plan your next adventure in Windsor nightlife.
From the first zing of a craft cocktail to the last clink of a tiki mug, the Windsor Cocktail Bar Crawl delivers an unforgettable night packed with flavor, flair, and friendship. Whether you’re a cocktail connoisseur or a social adventurer, this route through Chapel Street’s best bars guarantees excitement at every turn. Ready to raise your glass and explore Windsor’s vibrant after-dark scene? Grab your crew, pace yourself, and let each stop rewrite your expectations of a night out.
Crawl Map