đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant nightlife with our cocktail bar crawl! Visit 3 fantastic spots — Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar — for an unforgettable night of delicious drinks, great vibes, and good company. Perfect for food lovers and cocktail enthusiasts alike, this crawl combines the best pubs, bars, and event venues in town. Whether you're celebrating or just out for a fun evening, this is your chance to experience Windsor’s lively bar scene!
Last updated: July 2025
Get ready to ignite your night with a thrilling cocktail bar crawl right in the heart of Windsor’s Chapel Street. This curated route kicks off with Naughty Nancy’s, where live music fuels an electric atmosphere perfectly paired with crave-worthy bites. Next, the adventure shifts gears to Better Days Cocktail Bar—a vibrant playground of inventive drinks and retro games that sparks laughter and connection. Finally, the crawl lands at Blackwoods Wine & Cocktail Bar, where polished mixology meets inviting charm, wrapping up your night in style. Whether you’re rallying friends or seeking new social thrills, this crawl pulses with energy, flavor, and endless fun.
Kick off the night at Naughty Nancy’s, where infectious live music and hearty, flavor-packed dishes set a high-energy tone. This food-forward pub immerses you in a bustling scene that’s all about vibrant tastes and lively social buzz.
The next stop is a short stroll along Chapel Street, keeping the momentum alive as you head toward a spot brimming with playful spirit.
Better Days injects a fresh wave of fun with creative cocktails and a nostalgic twist—think video games and cozy corners—making it the perfect place to laugh, compete, and rejuvenate before the final leg.
The next stop is a brief, easy walk further down Chapel Street, transitioning you smoothly into the evening’s elegant finale.
Wrap up your crawl at Blackwoods, where expert mixology and a carefully curated wine list create an atmosphere that’s lively yet polished—ideal for savoring sophisticated drinks and celebrating a night well spent.
The next stop is your call—either linger here to soak in the last vibrant moments or explore Windsor’s nightlife further on your own terms.
This Windsor cocktail bar crawl delivers an unforgettable night packed with flavor, fun, and fantastic company. From the upbeat beats of Naughty Nancy’s to the playful spirit of Better Days and the refined charm of Blackwoods, every stop amps up the excitement. So gather your crew, pace yourself, and dive into a social adventure that captures the very best of Windsor’s Chapel Street nightlife. Cheers to an epic crawl!
Crawl Map