đź“… Open Today: Crawl likely open on Fridays
Explore Windsor’s vibrant nightlife with our cocktail bar crawl! Visit three fantastic venues — Ruelle Wine Bar, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar — each offering unique drinks, great food, and a lively atmosphere. Whether you’re into craft cocktails, fine wines, or just a fun night out, this crawl is perfect for discovering the best spots Windsor has to offer. Grab your friends and get ready for an unforgettable evening!
Last updated: July 2025
Kick off your Windsor night with an electrifying cocktail bar crawl designed to elevate your evening from the first sip to the last toast. This carefully curated journey begins at Ruelle Wine Bar, where a refined wine selection and artisanal snacks set a sophisticated, inviting tone. Next, amp up the energy at Better Days Cocktail Bar — a playground of inventive cocktails and lively games that fuel laughter and connection. Wrap up your expedition at Blackwoods Wine & Cocktail Bar, where expertly crafted drinks meet a dynamic yet approachable atmosphere, perfect for celebrating newfound friends and unforgettable moments. This crawl blends refinement, fun, and spirited social buzz across Windsor’s vibrant Chapel Street corridor, promising an adventurous night out packed with flavor and flair.
Ruelle Wine Bar kicks off the crawl with a sophisticated edge, offering a carefully curated wine list paired with gourmet cheeses and charcuterie that prime your palate and set an elegant tone for the night ahead.
The next stop is a short, vibrant stroll down Chapel Street, immersing you in Windsor’s buzzing nightlife scene as anticipation builds for the energetic vibe at Better Days Cocktail Bar.
Better Days injects a playful burst of energy into the crawl with its inventive cocktails, nostalgic games, and lively atmosphere—perfect for sparking laughter and social connection right in the heart of Chapel Street.
The next stop is a quick and easy walk just down the street, keeping the momentum alive as you head towards Blackwoods’ welcoming and spirited setting.
Blackwoods brings the crawl home with its expertly crafted cocktails and inviting ambiance, striking the perfect balance between lively energy and sophisticated comfort to cap off an adventurous night out.
The next stop is the end of the crawl, letting you savor the moment and the vibrant Windsor nightlife that surrounds you.
Ready to turn your Windsor night into a spirited adventure? This cocktail crawl weaves a perfect blend of refined tastes, playful vibes, and dynamic social scenes — all steps apart on Chapel Street. Whether you’re celebrating a special occasion or simply chasing great drinks and memorable company, these three bars promise an unforgettable journey. Gather your crew, map your route, and dive into Windsor’s cocktail culture like never before.
Crawl Map