đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s vibrant cocktail scene with our fun-filled bar crawl! Visit three fantastic venues — Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar — each offering unique drinks and great vibes. Perfect for anyone looking to enjoy a food-centric, pub-style night out with friends. Whether you're a cocktail connoisseur or just looking for a memorable evening, this crawl promises tasty drinks, lively atmospheres, and plenty of laughs. Cheers to a night you won't forget!
Last updated: July 2025
Kick off your night in Windsor with a cocktail crawl designed for thrill-seekers and social butterflies alike. This curated route takes you from the pulsating heart of live music and culinary delights at Naughty Nancy’s, through a spirited playground of games and inventive drinks at Better Days Cocktail Bar, and finishes strong with refined yet lively vibes at Blackwoods Wine & Cocktail Bar. Each stop ramps up the excitement and offers a fresh twist on Windsor’s vibrant nightlife, ensuring your evening flows seamlessly from one memorable experience to the next.
Launch your evening where dynamic live music meets robust flavors—Naughty Nancy’s sets an energetic tone with its vibrant crowd, bold cocktails, and a menu that keeps the party fueled. This hotspot’s buzzing atmosphere guarantees a lively start packed with rhythm and rich tastes.
The next stop is a short, spirited stroll down Chapel Street, keeping the energy high as you approach a haven of nostalgic fun and creative cocktails.
Shift gears into a vibrant lounge where playful vibes collide with expertly mixed drinks. Better Days invites you to dive into classic games and inventive cocktails, amplifying the social buzz and injecting a fresh wave of fun into the night.
The next stop is just a lively few minutes on foot, a perfect transition that builds anticipation for an elegant yet spirited finale.
Cap off your adventure at Blackwoods, where sophisticated sips meet an inviting atmosphere. This spot balances refined craft cocktails with convivial energy, making it the ideal culmination for your Windsor evening of exploration and connection.
The next stop is the conclusion of the crawl, conveniently located to leave you ready for whatever the night holds next.
This Windsor Cocktail Bar Crawl delivers a perfectly paced journey through some of the city’s most vibrant venues. Whether you’re chasing live beats, game-night laughs, or sleek cocktails, each stop elevates the night with its unique energy and social spark. Ready to own the night? Grab your crew, follow the trail, and make Windsor your playground for unforgettable cocktail adventures.
Crawl Map