đź“… Open Today: Crawl likely open on Fridays
Explore Windsor's vibrant nightlife with our cocktail bar crawl! Visit 3 fantastic spots including Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Perfect for foodies and drink lovers alike, this crawl combines delicious cocktails, lively atmospheres, and great company. Whether you're celebrating or just looking for a fun night out, this food-centric pub crawl is your ticket to Windsor's best bar scene. Cheers to good times!
Last updated: July 2025
Kick off your night on Windsor’s lively Chapel Street with a cocktail bar crawl packed with energy, flavor, and unforgettable social moments. This crawl is designed for the adventurous spirit eager to experience a dynamic mix of atmospheres—from the pulsating rhythms and hearty bites at Naughty Nancy’s, to the joyous playful spirit and inventive drinks at Better Days Cocktail Bar, culminating in the refined yet vibrant ambiance of Blackwoods Wine & Cocktail Bar. Each stop builds on the last, creating a seamless journey of discovery, fun, and expertly crafted libations that keep the night buzzing with excitement.
Launch your evening with Naughty Nancy’s infectious energy, where live music and innovative cocktails set a dynamic tone. This food-forward pub blends bold flavors with a vibrant crowd, making it the perfect starting point to fuel your night.
The next stop is a short, lively stroll along Chapel Street, letting you soak in Windsor’s buzzing nightlife atmosphere as anticipation builds.
Shift gears to a spirited playground of craft cocktails and nostalgic fun. Better Days invites you to unwind with board games and video classics while enjoying expertly mixed drinks, making socializing effortless and vibrant.
The next stop is a quick, energizing walk along Chapel Street, keeping the momentum alive as you move toward a more refined setting.
Cap off your crawl in style at Blackwoods, where expert craftsmanship meets an inviting yet polished atmosphere. This venue strikes the perfect balance between lively and sophisticated, making it an ideal place to toast to an epic night.
The next stop is the conclusion of the crawl, conveniently nestled nearby to close the night with elegance and flair.
This Windsor cocktail crawl captures the essence of Chapel Street’s nightlife—energetic, adventurous, and endlessly fun. Whether you’re chasing live music, playful vibes, or refined cocktails, these three hotspots deliver a night packed with flavor and friendship. Ready to own the night? Gather your crew, follow the flow, and make every sip count on this unforgettable Windsor bar adventure.
Crawl Map