đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant cocktail scene on this fun-filled bar crawl! Explore five unique venues, from the ship-themed Three Monkeys with its plush couches to the plant-filled Jungle Boy serving tiki mugs. Sip rum and creative cocktails in cosy, quirky spots perfect for a relaxed night out. Whether you're into lively DJ parties or intimate hangouts, this crawl offers a mix of stylish bars, cozy atmospheres, and unforgettable drinks. Perfect for anyone looking to spice up their Windsor night!
Last updated: July 2025
Kick off an electrifying night out in Windsor by embarking on this spirited cocktail bar crawl that threads together five of Chapel Street’s most exciting watering holes. From the infectious energy of Three Monkeys’ weekend DJ sessions to the playful charm of Better Days’ game-filled lounge, each stop amps up the fun with distinct personalities and craft cocktails that keep the buzz alive. As the crawl unfolds, revel in Blackwoods’ elegant yet unpretentious mixology, step into the immersive ship-inspired world of Holy Grail, and cap off your adventure with Jungle Boy’s tropical escape brimming with exotic flavors and lush greenery. This energetic route blends social connection, creative drinks, and lively atmospheres, making every step a fresh celebration of Windsor’s cocktail culture.
Launch your night at Three Monkeys, where intimate yet vibrant vibes set the tone with expertly crafted cocktails and weekend DJ beats that spark early energy and social buzz.
The next stop is a quick, lively stroll down Chapel Street to Better Days, where the atmosphere shifts from rhythmic beats to playful, interactive fun.
At Better Days, dive into a spirited mix of inventive cocktails and nostalgic gaming that fuels laughter and connection, perfectly balancing the crawl’s vibrant momentum with a touch of whimsical charm.
The next stop is a short, buzz-worthy walk along Chapel Street to Blackwoods, where the scene matures into sophisticated yet approachable elegance.
Blackwoods elevates the evening with refined cocktails and a curated wine list, offering a chic yet welcoming setting that heightens the crawl’s energetic pulse with stylish allure.
The next stop is a brisk, engaging stroll to Holy Grail, where the vibe welcomes you aboard a cozy, thematic escapade.
Step into Holy Grail’s ship-inspired haven, where plush seating and handcrafted cocktails invite lively conversations and group revelry, blending comfort with spirited fun as the crawl deepens.
The next stop is a short walk continuing the Chapel Street journey, leading you to Jungle Boy’s tropical lounge bursting with vibrant energy.
Conclude your adventure at Jungle Boy, where exotic cocktails in tiki mugs and lush plant-filled surroundings deliver a burst of tropical excitement, sending the night off with a bold, unforgettable flourish.
The next stop is the perfect spot to either continue your night or reflect on an exhilarating crawl well enjoyed.
Whether you’re a cocktail connoisseur or a social adventurer, this Windsor crawl on Chapel Street promises an unforgettable night brimming with inventive drinks, eclectic atmospheres, and dynamic vibes. So gather your crew, pace your sips, and let each bar reveal its unique flavor and energy—because this is more than a bar hop, it’s a celebration of Windsor’s spirited nightlife. Ready to dive in? Your next great night out starts here.
Crawl Map