đź“… Open Today: Crawl likely open on Fridays
Explore Windsor's vibrant nightlife with our cocktail bar crawl featuring three fantastic venues: Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Perfect for food and drink lovers, this crawl offers a fun, social way to discover the best bars, pubs, and restaurants in town. Whether you're after creative cocktails, a lively pub vibe, or a cozy wine experience, this 3-venue tour has it all. Grab your friends and get ready for a memorable night out!
Last updated: July 2025
Dive headfirst into Windsor’s buzzing nightlife with an exhilarating cocktail bar crawl that pulses with energy and flavor. This carefully curated journey along Chapel Street kicks off at Naughty Nancy’s, where live music and bold, food-centric flavors set a spirited tone. Next, channel your inner child and ignite friendly competition with classic board and video games at Better Days Cocktail Bar, where inventive drinks and playful vibes elevate the mood. Finally, settle into the refined yet vibrant atmosphere of Blackwoods Wine & Cocktail Bar, where expert mixology and a welcoming crowd create the perfect finale. Each stop offers its own unique rhythm, ensuring your night flows from lively beats to clever cocktails and unforgettable connections.
Kick off your crawl at Naughty Nancy’s, a spirited pub alive with live music and palate-pleasing dishes that fuel the night’s energy and set a bold, welcoming tone.
The next stop is a short, vibrant stroll down Chapel Street, keeping the lively atmosphere buzzing as you head to your playful second venue.
Shift gears into a fun, interactive vibe where inventive cocktails meet board games and nostalgic video games, perfect for sparking laughter and social connections.
The next stop is just a quick walk along Chapel Street, allowing the night’s energy to build smoothly toward a sophisticated yet lively finale.
Wrap up the crawl at Blackwoods, where expert craft cocktails and an elegantly approachable vibe offer a stylish, energetic close to your Windsor adventure.
The next stop is the conclusion of your crawl, just a few steps away from the heart of Chapel Street’s vibrant nightlife.
From live rhythms and hearty bites to playful games and refined cocktails, this Windsor crawl delivers a night packed with energy, flavor, and memorable moments. Whether you’re meeting friends or making new ones, soak in the vibrant pulse of Chapel Street’s best bars and raise your glass to an unforgettable social adventure. Ready to dive in? The night is calling.
Crawl Map