📅 Open Today: Crawl likely open on Saturdays
Discover Windsor’s best cocktail bars on this fun-filled crawl! Visit three top venues — Pre Drinks Bar, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar — each offering unique drinks, lively atmospheres, and plenty of chances to dance, sing karaoke, or just relax with friends. Perfect for foodies, night owls, and anyone looking for a memorable night out in Windsor. Cheers to good times and great cocktails!
Last updated: June 2025
Dive into a buzzing cocktail adventure through Windsor's coolest spots, where every drink feels like a story waiting to unfold and each stop cranks up the excitement. Start at Pre Drinks Bar, a lively hangout packed with energy and a food menu that keeps things fueled and fun. Next, swing over to Better Days Cocktail Bar for its creative cocktails and nostalgic games that spark laughs and connections. Finally, end at Blackwoods Wine & Cocktail Bar, a spot that's elegant but easygoing, with top-notch mixes and an vibe perfect for deep chats and memorable toasts. This crawl blends different vibes and flavors for a night full of good times, tasty sips, and that social spark.
We kick off this crawl with some serious high-energy fun at Pre Drinks Bar. It's got a vibrant setup, pumping music, and a food-focused menu that keeps the party going and everyone chatting.
The next spot is just a quick, lively walk down Chapel Street, easing into a more playful and intimate vibe.
Better Days Cocktail Bar brings a playful twist to the crawl, with inventive drinks and classic video games or board games that get people interacting and sharing laughs.
The next one is only a few steps away, keeping the energy rolling as you move to a smoother, more refined scene.
Blackwoods caps off the night with a classy yet approachable feel, offering expertly made cocktails and a great wine selection that encourages laid-back conversations and fun toasts.
This is where the crawl wraps up, ideally set for extending your night in Windsor's scene or just enjoying a solid, satisfying end to the adventure.
Eager to spark your evening in Windsor? This cocktail bar crawl is your easy ticket to a night of killer drinks, vibrant energy, and fresh connections. Whether you're with friends or going solo, each stop draws you into the city's mix of nightlife gems. So, round up your crew, keep those sips in check, and let Windsor's spots surprise you with their charm and flair.
Crawl Map