đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant nightlife with our cocktail bar crawl featuring three fantastic spots: Ruelle Wine Bar, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Perfect for wine lovers and cocktail enthusiasts alike, this crawl offers a mix of delicious drinks, lively atmospheres, and great company. Whether you're after a classy wine experience or creative cocktails, this 3-venue adventure is your ticket to a memorable night out in Windsor!
Last updated: July 2025
Dive into Windsor’s cocktail culture with a dynamic crawl designed for those who crave a night packed with flavor, fun, and social spark. Begin your adventure at Ruelle Wine Bar, where intimate charm and a world-class wine selection set the tone for an unforgettable evening. Next, shift gears into playful mode at Better Days Cocktail Bar, a hotspot where craft cocktails meet retro gaming for a contagious buzz of excitement and nostalgia. Conclude your journey at Blackwoods Wine & Cocktail Bar, a stylish yet inviting venue that masters the art of blending lively energy with expert mixology. This crawl flows seamlessly from sophisticated sips to spirited playfulness and ends on an exhilarating high note — perfect for friends, couples, or anyone ready to conquer Windsor’s cocktail scene.
Kick off the night at Ruelle Wine Bar, where a curated wine list and artisanal small plates create a refined yet inviting atmosphere that primes your palate for the evening ahead.
The next stop is a brief, lively stroll along Chapel Street, taking you from the intimate wine retreat to a buzzing hub of playful cocktail energy.
Better Days amps up the adventure with inventive cocktails and a nostalgic twist—think classic video games projected on the wall—perfect for sparking camaraderie and laughter.
The next stop is a quick walk down Chapel Street, keeping the momentum alive as you head to a bar known for effortlessly blending elegance with vibrant vibes.
Close out the crawl at Blackwoods, where a masterful cocktail menu and a lively yet sophisticated setting ensure your night ends on a high, energizing note.
The next stop is the conclusion of the crawl, leaving you perfectly positioned to either continue exploring Windsor’s nightlife or reflect on an epic evening.
From the refined beginnings at Ruelle to the spirited interlude at Better Days and the elevated finale at Blackwoods, this Windsor cocktail crawl promises a night of nonstop social adventure and flavor exploration. Rally your crew, put on your party shoes, and let this curated route ignite your evening with unforgettable cocktails and contagious energy. Ready for your next great night out? Windsor’s best bars are waiting.
Crawl Map