đź“… Open Today: Crawl likely open on Fridays
Ready for a fun night out in Windsor? Join our cocktail bar crawl through three fantastic venues: Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Discover a snug, quirky neighborhood hangout scene with great beers, inventive cocktails, and lively DJ parties on weekends. Perfect for anyone looking to sip, socialize, and dance the night away in a friendly, vibrant atmosphere. Your memorable Windsor nightlife adventure starts here!
Last updated: July 2025
Windsor’s Chapel Street pulses with energy, making it the perfect playground for a cocktail bar crawl that’s anything but ordinary. Kick off your night at Three Monkeys, where infectious beats and expertly mixed drinks set a spirited tone. From there, shift gears to Better Days Cocktail Bar, a lively hub where nostalgia meets inventive cocktails — complete with classic games that spark camaraderie and laughter. Finish strong at Blackwoods Wine & Cocktail Bar, where polished yet unpretentious vibes invite you to savor finely crafted cocktails in a welcoming atmosphere. This crawl is designed to keep your social adventure flowing seamlessly, amplifying excitement with every step and sip.
Launching the crawl with infectious energy, Three Monkeys combines lively weekend DJ sessions with expertly mixed cocktails, igniting the night with rhythm and flavor right from the start.
The next stop is a quick, vibrant stroll along Chapel Street to Better Days Cocktail Bar, keeping the momentum alive with sights and sounds that match the night’s energy.
Injecting playful spirit into the crawl, Better Days invites you to unwind with inventive cocktails amid nostalgic video games and warm social vibes, sparking laughter and connection.
The next stop is an easy, lively walk along Chapel Street to Blackwoods Wine & Cocktail Bar, elevating the evening’s sophistication while staying rooted in Chapel Street’s vibrant scene.
Closing out the night, Blackwoods offers a polished yet inviting atmosphere where expertly crafted cocktails and attentive service create the perfect setting for memorable conversations and stylish socializing.
The next stop is the conclusion of this dynamic crawl, leaving you perfectly positioned to continue exploring Windsor’s nightlife or to savor the night’s last moments right here.
This Windsor cocktail bar crawl delivers a dynamic journey through Chapel Street’s most vibrant social spots. Each stop builds on the last — from energizing beats and lively games to sophisticated sips — crafting an adventurous night out that’s packed with fun, flavor, and unforgettable connections. Ready to dive in? Gather your crew, pace your pours, and let Windsor’s spirited cocktail scene lead you through a night of pure excitement.
Crawl Map