đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant cocktail scene on our fun-filled pub crawl! Explore five fantastic venues including Naughty Nancy's, Better Days Cocktail Bar, Blackwoods Wine & Cocktail Bar, Holy Grail, and Jungle Boy. From ship-themed rum & cocktail spots to cozy tiki mugs and stylish lounges, you'll enjoy a variety of food-centric, pub, and event venues. Perfect for a lively night out with friends, delicious drinks, and great vibes. Let’s make your evening unforgettable!
Last updated: July 2025
Get ready to ignite your night on Windsor’s iconic Chapel Street with a cocktail bar crawl that pulses with energy, creativity, and social buzz. This carefully curated route kicks off amidst the lively buzz of Naughty Nancy’s, where bold flavors and live music set the perfect tone for adventure. From there, the vibe shifts to playful sophistication at Better Days, a haven for cocktail lovers and game enthusiasts alike. Blackwoods then elevates the experience with polished mixology and a welcoming atmosphere that fits any occasion. As the evening unfolds, Holy Grail’s ship-inspired setting offers a cozy yet vibrant spot to savor expertly crafted rum cocktails. Finally, cap off your night at Jungle Boy, a tropical oasis where exotic drinks in quirky tiki mugs and lush surroundings celebrate the art of fun. This crawl isn’t just about bars—it’s a journey through evolving moods and social moments, guaranteeing a night packed with excitement and memorable sips.
Kick off the night amidst Naughty Nancy’s energetic blend of live music and craft cocktails, where hearty bites fuel your fun and set an infectious pace for the evening ahead.
The next stop is a short, vibrant stroll down Chapel Street, keeping the energy high as you approach your next cocktail haven.
Shift gears into a playful, welcoming vibe at Better Days, where inventive cocktails meet retro gaming for a lively social playground that sparks laughter and connection.
The next stop is a quick and lively walk along Chapel Street, maintaining momentum as the night’s flavors deepen.
Blackwoods invites you to savor expertly crafted cocktails and a curated wine list in a stylish yet inviting setting, elevating the night with refined tastes and warm conversations.
The next stop is a brief walk that transitions the night toward a unique thematic escape on Chapel Street.
Step aboard Holy Grail’s ship-inspired bar, where plush seating and a stellar rum selection create the perfect scene for spirited chats and cocktail craftsmanship.
The next stop is a short stroll that brings you closer to a lush, tropical finale to crown the evening.
Conclude your crawl surrounded by jungle greenery and exotic tiki cocktails at Jungle Boy—a vibrant, spirited sanctuary that turns up the fun and flavor for a memorable nightcap.
The crawl ends here, leaving you perfectly positioned to continue your night or head out with a fresh buzz and great memories.
This Windsor Cocktail Bar Crawl delivers a night bursting with character, creativity, and contagious energy. From live music and hearty bites to tropical tiki vibes and refined cocktails, each stop promises a new adventure in flavor and fun. Lace up your walking shoes, gather your crew, and dive into Windsor’s spirited nightlife scene—where every sip tells a story and every moment is charged with excitement. Ready to own the night? Let the crawl begin!
Crawl Map