đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's best cocktail bars on this fun-filled crawl! Visit three fantastic venues—Death or Glory, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—and enjoy expertly crafted drinks, lively atmospheres, and great company. Perfect for an unforgettable night out with friends, this crawl combines the best of Windsor’s bar scene with a friendly, energetic vibe. Cheers to good times and great cocktails!
Last updated: July 2025
Kick off your night in Windsor with a cocktail bar crawl that pulses with energy and social spark. From the first sip at Death or Glory’s craft-driven bar to the playful atmosphere of Better Days Cocktail Bar packed with nostalgic games, this crawl invites you to blend excitement, flavor, and friendly competition. As the night builds, Blackwoods Wine & Cocktail Bar wraps up the adventure with expert mixology and a buzzing crowd, delivering the perfect finale to an unforgettable night out on Chapel Street. Whether you’re chasing inventive cocktails, engaging company, or vibrant atmospheres, this crawl is your passport to Windsor’s most lively and spirited watering holes.
Starting your crawl at Death or Glory sets an energetic tone with its masterful craft cocktails and buzzing atmosphere. This spot’s dynamic vibe and welcoming staff create the perfect launchpad for a night of bold flavors and social buzz.
The next stop is a brief, vibrant stroll down Chapel Street, keeping the energy flowing as you move into a playful and interactive setting.
Better Days amplifies the adventure with its blend of inventive cocktails and lively game-filled buzz. It’s a social playground where nostalgic video games meet craft mixology, fueling laughter and camaraderie that elevate the night’s momentum.
The next stop is a short, spirited walk along Chapel Street, priming you for a smooth transition into an elegant yet vibrant finale.
Closing the crawl at Blackwoods Wine & Cocktail Bar offers a refined yet lively atmosphere where expert cocktails meet a welcoming crowd. It’s the perfect spot to savor sophisticated flavors while soaking up Windsor’s electric nightlife energy.
The next stop is the end of the crawl, leaving you perfectly positioned to continue your night or reflect on an exhilarating adventure.
Wrap up your Windsor cocktail bar crawl with memories of bold flavors, spirited games, and vibrant social scenes. Each stop crafts a distinct chapter in your night’s story, making this crawl the definitive way to experience Chapel Street’s dynamic cocktail culture. Ready for your next round? Windsor’s nightlife awaits your return with even more adventures just around the corner.
Crawl Map