đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s best cocktail scene with our lively bar crawl! Visit three fantastic venues—Ruelle Wine Bar, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering unique drinks, great vibes, and tasty food. Perfect for anyone looking to enjoy a night of drinks, good company, and local flavor. Whether you're into wine, cocktails, or just a fun night out, this crawl is your ticket to Windsor’s vibrant bar scene!
Last updated: July 2025
Dive headfirst into Windsor’s energetic cocktail culture with a crawl that balances sophisticated sips and spirited social adventures. Begin your night at Ruelle Wine Bar, where a refined wine selection paired with artisanal cheeses sets the stage for connection and conversation. From there, amp up the excitement at Better Days Cocktail Bar, a lively playground boasting inventive cocktails and nostalgic games that spark laughter and friendly competition. Finally, let the crawl culminate at Blackwoods Wine & Cocktail Bar, a dynamic hotspot where expertly crafted drinks meet an inviting atmosphere perfect for group celebrations or intimate rendezvous. This crawl is designed for those who crave a night packed with flavor, fun, and unforgettable memories.
Kick off your evening with Ruelle Wine Bar’s sophisticated charm—a sanctuary of curated wines and gourmet pairings that primes your palate and sparks engaging chatter.
The next stop is a quick, vibrant stroll along Chapel Street, transitioning from wine-focused elegance to playful cocktail innovation at Better Days.
Inject energy into the night at Better Days, a lively spot where inventive cocktails meet board games and video classics—perfect for sparking connections and playful competition.
The next stop is a short walk down Chapel Street, shifting gears toward a crowd-pleasing cocktail haven with a buzzing yet welcoming atmosphere at Blackwoods.
Conclude your crawl at Blackwoods, where expertly crafted cocktails and a lively ambiance create the perfect backdrop for celebrating new friendships and savoring every moment.
The next stop is the finale—no more walking, just settling in to enjoy the vibrant Windsor nightlife on a high note.
Ready to embrace Windsor’s cocktail culture in full throttle? This crawl ensures every stop delivers a fresh wave of excitement, from refined beginnings to playful middle acts and a spirited finale. Gather your crew, pace your sips, and get set for an unforgettable night where every cocktail tells a story and every laugh echoes down Chapel Street. Your Windsor adventure awaits—cheers to the night!
Crawl Map