đź“… Open Today: Crawl likely open on Fridays
Join us in Windsor for a lively cocktail bar crawl through three of the coolest spots: Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Perfect for those who love snug, quirky neighbourhood hangouts with a mix of craft cocktails, beer, and weekend DJ parties. Whether you're after a relaxed evening or a lively dance floor, this crawl offers great drinks, fun atmospheres, and great company. Get ready for an unforgettable night out!
Last updated: July 2025
Windsor’s Chapel Street comes alive after dark with a cocktail bar crawl designed for adventurers craving bold flavors and social buzz. Kick off your night at Three Monkeys, where infectious energy and weekend DJ sets set the perfect tone. The journey continues at Better Days Cocktail Bar, a playground of inventive drinks and playful nostalgia that invites you to unleash your competitive side over board games and classic video games. Wrap up the evening at Blackwoods Wine & Cocktail Bar, where polished cocktails meet an inviting atmosphere, providing the ideal backdrop to celebrate new friendships or flirt with the night’s magic. Each stop offers a fresh pulse, crafting an unstoppable rhythm that keeps the night vibrant and the spirits high.
Launching the crawl with its dynamic mix of quirky charm and weekend DJ energy, Three Monkeys instantly electrifies the night and sets a high-spirited social tone.
The next stop is a short, lively stroll along Chapel Street, keeping the momentum flowing effortlessly.
This stop amps up the fun with inventive cocktails and a playful vibe fueled by retro games and interactive entertainment, sparking friendly competition and laughter.
The next stop is just a brief, engaging walk down Chapel Street, maintaining the vibrant energy as you head toward a more refined finale.
Capping the crawl with an elegant yet lively atmosphere, Blackwoods offers expertly crafted cocktails and a welcoming space perfect for toasting to the night’s adventures.
The next stop is the end of the crawl—no walking required, just savoring the final moments of an exhilarating night.
Ready to unleash your inner cocktail explorer? This Windsor crawl threads together vibrant beats, playful competition, and sophisticated sips, delivering an unforgettable night out. Gather your crew, follow the rhythm down Chapel Street, and let each bar’s unique energy propel your adventure. Cheers to unforgettable connections and stories that start with one epic sip!
Crawl Map