đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant cocktail scene with our curated pub crawl! Explore five fantastic venues including Naughty Nancy's with its ship-themed cozy vibe, the contemporary Jungle Boy with tiki mugs, and other hotspots like Better Days, Blackwoods, and Holy Grail. Whether you love rum, inventive cocktails, or classic drinks, this crawl offers a perfect mix of food-centric pubs, stylish bars, and lively nightspots. Get ready for a memorable night of great drinks, good company, and Windsor’s best bar vibes!
Last updated: July 2025
Embark on an adventurous evening through Windsor’s iconic Chapel Street, where every stop in this cocktail bar crawl amps up the energy, flavor, and social buzz. This journey kicks off with Naughty Nancy’s infectious live music and food-forward drinks, setting a spirited tone that’s impossible to resist. Next, roll into a playful atmosphere at Better Days Cocktail Bar, where retro games and inventive cocktails spark shared laughs and friendly competition. The tempo shifts to sophisticated yet approachable at Blackwoods Wine & Cocktail Bar, where fine wines and masterful mixes create a perfect balance of elegance and liveliness. From there, step aboard the ship-themed Holy Grail, a cozy yet vibrant spot that celebrates rum and handcrafted cocktails in a unique setting. Finally, cap off your night in tropical style at Jungle Boy, where lush greenery and bold tiki concoctions deliver an unforgettable finale. This crawl isn’t just about drinks—it’s a curated social adventure that pulses with excitement from start to finish.
Kick off the crawl at Naughty Nancy’s, where live music energizes the crowd and bold, food-centric cocktails fuel your night. Its vibrant atmosphere and hearty dishes lay the perfect foundation for an adventurous evening.
The next stop is a short and lively stroll down Chapel Street, keeping the momentum flowing with the buzz of nearby shops and street life.
Step into Better Days for a playful vibe where inventive cocktails meet retro video and board games, sparking shared excitement and laughter that energizes the crawl’s social spirit.
The next stop is a quick and engaging walk further along Chapel Street, where anticipation builds for a shift toward refined flavors.
Blackwoods elevates the evening with its curated wine list and expertly crafted cocktails, offering a lively yet polished atmosphere that balances the crawl’s playful energy with sophistication.
The next stop is an inviting short stroll, allowing the night’s vibrant energy to seamlessly transition into a unique themed experience.
Holy Grail docks you into a ship-inspired sanctuary where smooth rums and attentive cocktail craftsmanship create a cozy yet spirited setting, perfect for gathering with friends and deepening the night’s vibe.
The next stop is an easy walk that shifts the scene toward tropical flair and exotic cocktail artistry.
Conclude the crawl at Jungle Boy, where lush greenery and daring tiki cocktails in signature mugs deliver a high-energy tropical escape, igniting the final burst of fun and flavor for the night.
The crawl’s last stop means it’s time to unwind or keep the party rolling as you soak in Jungle Boy’s vibrant, plant-filled atmosphere.
This Windsor Cocktail Bar Crawl is your ticket to an unforgettable night alive with diverse flavors, buzzing energy, and inviting social vibes. Whether you’re a cocktail connoisseur or an adventurous night owl, these five stops will keep your spirits soaring and your conversations flowing. Grab your crew, map out your route, and dive into the pulse of Chapel Street—because when cocktails and character collide, every sip tells a story. Cheers to the night ahead!
Crawl Map