đź“… Open Today: Crawl likely open on Fridays
Join us in Windsor for an unforgettable cocktail bar crawl! Explore three fantastic venues—Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar—each offering unique drinks and vibrant atmospheres. Perfect for food lovers and cocktail enthusiasts alike, this crawl blends great drinks, lively vibes, and a friendly crowd. Whether you're celebrating or just out for a good time, this pub crawl is your ticket to Windsor’s best bar scene.
Last updated: July 2025
Dive headfirst into an exhilarating Windsor night on Chapel Street, where every stop promises a fresh surge of energy and style. Kick off at Naughty Nancy’s, where the air pulses with live music and bold flavors, setting a vibrant tone for the evening. Next, shift gears to Better Days Cocktail Bar, a playful hotspot blending inventive cocktails with nostalgic games, sparking laughter and connection. Finish strong at Blackwoods Wine & Cocktail Bar, where expertly crafted drinks and a chic yet inviting atmosphere invite you to savor the night’s crescendo. This crawl is your ticket to a lively social adventure, where every sip tells a story and every stop amps up the fun.
Naughty Nancy’s ignites the crawl with its energetic blend of live music and hearty, flavor-packed dishes, creating an upbeat launchpad for the night ahead.
The next stop is just a short, lively stroll along Chapel Street, keeping the energy flowing as you move toward your next cocktail adventure.
Better Days amps up the fun with its quirky mix of inventive cocktails and classic games, injecting playful competition and shared laughs into the evening’s rhythm.
The next stop is a quick, vibrant walk down Chapel Street, maintaining the buzz as you head to an elegant finale.
Blackwoods brings the night to a sophisticated peak with expertly crafted cocktails and a warm, stylish atmosphere perfect for savoring every last drop.
The next stop is the grand finale of the crawl, so this is where you settle in and soak up the vibrant Windsor nightlife vibes.
Wrap up your Windsor Cocktail Bar Crawl with memories of bold flavors, playful moments, and stylish sips. Whether you’re new to Chapel Street or a local chasing fresh thrills, this curated journey guarantees an electric night packed with social sparks and spirited discovery. Ready to claim your spot on the crawl? Gather your crew, charge your night, and let Windsor’s cocktail scene sweep you off your feet.
Crawl Map