đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's best cocktail bars on this lively crawl! Visit three fantastic venues — Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar — each offering unique drinks, vibrant atmospheres, and delicious food. Perfect for a night out with friends, our crawl combines great drinks, good vibes, and memorable moments. Whether you're a cocktail connoisseur or just looking for a fun evening, this pub crawl is your ticket to Windsor's top spots!
Last updated: July 2025
Windsor’s cocktail scene pulses with energy and adventure, and this crawl is your passport to the best social buzz in town. Start strong at Naughty Nancy’s, where the air hums with live music and hearty, flavor-packed bites set the tone for a night of spirited fun. From there, slip into the playful charm of Better Days Cocktail Bar, where nostalgic games and inventive cocktails spark laughter and connection. Finally, wind down with a touch of sophistication at Blackwoods Wine & Cocktail Bar, where expert mixology meets a welcoming vibe that keeps the night alive and electric. This crawl is a curated journey through diverse atmospheres, each stop fueling a seamless flow of excitement and conviviality along Chapel Street.
Launch your night with Naughty Nancy’s vibrant energy: live tunes, craft cocktails, and a food-forward menu that ignites the party spirit right from the get-go.
The next stop is a brief, lively stroll down Chapel Street, keeping the momentum flowing as you head to a spot mixing nostalgia with cocktail creativity.
Shift gears into playful sophistication at Better Days, where cozy seating, retro games, and inventive drinks cultivate a fun and social atmosphere perfect for making memories.
The next stop is just a short walk further along Chapel Street, transitioning smoothly toward a refined yet approachable cocktail experience.
Cap off your adventure at Blackwoods, where expert cocktails and a polished yet welcoming vibe invite you to savor the night’s final moments in style.
The next stop is the conclusion of the crawl—you’re perfectly positioned to keep the night going or wind down with satisfaction.
This Windsor Cocktail Bar Crawl is your ultimate recipe for an unforgettable night of discovery, dynamic vibes, and crafted cocktails. Whether you’re rallying friends or meeting new ones, each stop amps up the excitement and delivers distinct flavors and experiences. So lace up your walking shoes, bring your adventurous spirit, and let Windsor’s Chapel Street be your playground for the night. Cheers to the thrill of the crawl!
Crawl Map