đź“… Open Today: Crawl likely open on Fridays
Ready for a night of sipping and socialising? Explore Windsor’s vibrant cocktail scene with our 3-venue crawl! Starting at Naughty Nancy’s, then onto Better Days Cocktail Bar, and finishing at Blackwoods Wine & Cocktail Bar, you'll enjoy a mix of creative drinks, lively atmospheres, and great company. Perfect for foodies and bar lovers alike, this crawl is your ticket to a fun-filled evening in Windsor’s best spots. Cheers to a memorable night out!
Last updated: July 2025
Kick off an unforgettable evening on Windsor’s iconic Chapel Street with a cocktail bar crawl that pulses with energy, flavor, and social buzz. This crawl launches at Naughty Nancy’s, where hearty dishes meet live music, setting an exhilarating tone. Next, slide into Better Days Cocktail Bar’s playful world of inventive drinks and nostalgic games, ramping up the fun and connection. Finally, wind down in style at Blackwoods Wine & Cocktail Bar, a sophisticated yet inviting spot perfect for toasting to new memories. Whether you're out with friends or starting a night of adventure, this crawl crafts the perfect rhythm of excitement and camaraderie to keep your spirits soaring all night long.
Naughty Nancy’s bursts with lively energy and robust flavors, making it the perfect launchpad for the crawl. Its dynamic mix of live music and food-centric cocktails fuels the night’s momentum, inviting you to dive headfirst into Windsor’s buzzing scene.
The next stop is a short, vibrant stroll down Chapel Street, keeping the energy flowing through Windsor’s lively heartbeat.
Better Days injects playful charm into the crawl with inventive cocktails paired with nostalgic board games and video games. It’s the perfect spot to spark laughter and friendly competition, elevating the social adventure to a new level.
The next stop is a quick, buzzing walk further along Chapel Street, perfect for catching your breath while staying in the groove.
Blackwoods rounds out the crawl with a sophisticated yet welcoming atmosphere. Its masterful cocktails and curated wine list offer a refined finish, letting you savor the night’s highlights while enjoying a warm, energetic crowd.
The next stop concludes the crawl here, so no more walking—just pure celebration.
Wrap up your Windsor cocktail bar crawl with a satisfied smile and new stories to tell. Each venue delivers a unique flavor of Chapel Street’s vibrant nightlife, blending music, games, and masterful drinks into one seamless adventure. Ready to own the night? Gather your crew and set out to conquer this spirited crawl — Windsor’s cocktail scene awaits your energy and appetite for fun.
Crawl Map