đź“… Open Today: Crawl likely open on Fridays
Discover Windsor's vibrant cocktail scene with our exclusive bar crawl featuring three fantastic venues: Naughty Nancy's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Perfect for food lovers and cocktail enthusiasts alike, this crawl offers a mix of delicious drinks, lively atmospheres, and great company. Whether you're celebrating or just out for a good time, explore the best bars, pub vibes, and hidden gems in Windsor—all in one epic night!
Last updated: July 2025
Windsor’s Chapel Street pulses with nightlife excitement, and this cocktail bar crawl captures its electric spirit perfectly. Kick off your evening where lively beats and hearty flavors set the tone at Naughty Nancy’s, mixing craft cocktails with an energetic crowd. Next, dive into friendly competition and inventive drinks at Better Days Cocktail Bar, where vintage gaming meets fresh cocktail artistry. Wrap up your night at Blackwoods Wine & Cocktail Bar, an inviting spot that balances lively conversation with expertly crafted drinks. This crawl is a seamless journey through Windsor’s most dynamic cocktail scenes—each stop delivering its own spark to keep your night soaring.
Naughty Nancy’s kicks off the crawl with an electric blend of live music energy and bold craft cocktails, setting an invigorating pace that energizes the night.
The next stop is a quick, lively stroll along Chapel Street, keeping the momentum as you head to Better Days Cocktail Bar.
Better Days infuses playful vibes with its quirky mix of retro games and inventive cocktails, inviting you to raise the fun factor and connect over friendly competition.
The next stop is a brief and upbeat walk down Chapel Street, perfect for chatting over your latest cocktail and gearing up for the finale.
Blackwoods delivers a sophisticated yet vibrant finale with expertly crafted cocktails and a curated wine list, wrapping the night in style and spirited conversation.
The next stop concludes the crawl here, offering a memorable spot to savor your last drink and reflect on an adventurous night.
Ready to light up your night? This Windsor cocktail crawl offers a thrilling blend of live energy, playful fun, and refined indulgence, all within a few spirited steps on vibrant Chapel Street. Gather your crew, embrace the buzz, and explore Windsor’s cocktail scene like never before—your next unforgettable night out starts here.
Crawl Map