đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant cocktail scene with our exclusive bar crawl! Visit three fantastic venues—Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering unique drinks and lively atmospheres. Perfect for food lovers and cocktail enthusiasts alike, this crawl is your chance to enjoy great drinks, good company, and the best spots Windsor has to offer. Grab your friends and get ready for a memorable night!
Last updated: July 2025
Kick off your night in Windsor with an electric cocktail bar crawl that pulses with energy and discovery. This curated journey along iconic Chapel Street sparks from the upbeat, food-centric buzz of Naughty Nancy’s, where live music and inventive drinks set a lively tone. Next, shift gears into playful charm at Better Days Cocktail Bar — a hotspot where craft cocktails meet nostalgic video games, making every sip a shared adventure. Finally, wind down your crawl at Blackwoods Wine & Cocktail Bar, a stylish yet inviting haven perfect for toasting to new memories with expertly crafted cocktails and a welcoming crowd. This crawl isn’t just about drinks — it’s a dynamic social expedition through Windsor’s spirited nightlife.
Launching the night with an energetic vibe, Naughty Nancy’s pulses with live music and hearty, flavor-packed bites that complement its inventive cocktails, setting a vibrant scene for the adventure ahead.
The next stop is a brief and lively stroll down Chapel Street, keeping the energy high as you move toward a more playful and intimate setting.
Here, the mood shifts to a spirited and social lounge filled with nostalgic gaming and playful cocktails, perfect for connecting over laughs and shared fun before the night’s crescendo.
The next stop is just a short walk along the buzzing Chapel Street, building anticipation for a refined yet inviting finale.
Closing the crawl with polished charm, Blackwoods offers expertly crafted cocktails and a warm atmosphere, elevating the night with a sophisticated yet unpretentious vibe perfect for lingering conversations and celebrations.
The crawl concludes here, within easy reach of Windsor’s lively streets, leaving you perfectly poised to continue your night or reflect on a memorable cocktail journey.
From the pounding rhythms of live music to nostalgic game nights and elegant cocktail craftsmanship, this Windsor crawl packs every moment with excitement and connection. Whether rallying with friends or diving into the local scene, these three stops deliver a seamless night of spirited adventure. Ready to taste Windsor’s cocktail heartbeat? Lace up your shoes and let the good times roll!
Crawl Map