đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant cocktail scene with our fun-filled bar crawl! Explore three unique venues—Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering a snug, quirky neighbourhood hangout with fantastic drinks. Perfect for a relaxed evening or a lively party, especially on weekends when DJ nights light up the vibe. Whether you're into creative cocktails or cool wine spots, this crawl promises a memorable night out with friends. Cheers to good times!
Last updated: July 2025
Windsor’s Chapel Street pulses with a dynamic cocktail scene that invites you to dive headfirst into an evening of vibrant energy and endless social adventure. This carefully curated crawl launches at Three Monkeys, a snug yet buzzing spot where rhythmic DJ sets and expertly mixed drinks set the tone for a night full of laughs and lively connections. Next, immerse yourself in the playful spirit of Better Days Cocktail Bar, where inventive cocktails meet retro video games, creating a spirited playground for all kinds of night owls. The finale lands at Blackwoods Wine & Cocktail Bar, a refined yet inviting venue perfect for savoring elegant drinks and sharing moments with your crew. Together, these stops craft an exhilarating arc—from upbeat beats through nostalgic fun to polished sophistication—that captures the essence of Windsor’s electric nightlife.
Starting strong, Three Monkeys amps up the night with its energetic DJ sessions and expertly crafted cocktails, creating an intimate yet spirited setting that sparks social vibes and gets the party rolling.
The next stop is a short and lively stroll along Chapel Street, keeping the momentum alive as you head toward the playful atmosphere of Better Days Cocktail Bar.
Better Days injects a dose of fun with its cozy couches, nostalgic video games, and inventive cocktail menu, inviting you to share laughs and friendly competition while maintaining the crawl’s vibrant energy.
The next stop is just a brief, upbeat walk down Chapel Street, transitioning the vibe toward Blackwoods’ more refined yet welcoming setting.
Blackwoods rounds out the crawl by blending lively camaraderie with polished sophistication, offering a spacious, stylish ambiance where you can savor expertly mixed cocktails and toast to a night well spent.
The next stop is the end of the crawl, perfectly located to let you linger and soak in Windsor’s vibrant after-hours scene.
This Windsor cocktail bar crawl is your passport to a night brimming with energy, creativity, and unforgettable social moments. Whether you’re chasing infectious beats, playful nostalgia, or elegant sips, each stop elevates your adventure along Chapel Street. Grab your crew, pace yourself through these spirited venues, and let Windsor’s dynamic nightlife show you a bold, flavorful side of the city you’ll want to revisit again and again.
Crawl Map