đź“… Open Today: Crawl likely open on Fridays
Ready for a night of fun in Windsor? Our cocktail bar crawl takes you through three fantastic spots: Don's, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Explore a food-centric, lively scene with expertly crafted drinks, delicious bites, and great vibes. Perfect for anyone looking to enjoy a memorable evening with friends, try new cocktails, and soak up the local bar scene. Cheers to a night you won't forget!
Last updated: June 2025
Kick off your night in Windsor with a cocktail bar crawl that amps up the energy and keeps the good times flowing. Begin at Don’s, where gourmet food meets a dynamic wine and cocktail selection, setting a flavorful foundation for the adventure ahead. Then, glide over to Better Days Cocktail Bar, where nostalgia meets inventive mixology amidst playful vibes and interactive games—perfect for sparking laughter and new connections. Cap the night at Blackwoods Wine & Cocktail Bar, a spirited hotspot blending expertly crafted cocktails with a welcoming atmosphere that invites everyone to celebrate. This crawl is designed for those chasing vibrant scenes, bold flavors, and unforgettable social moments in the heart of Windsor.
Start your evening at Don’s, where a lively atmosphere and food-centric approach energize the night. The house-made focaccia and standout fried chicken sandwich pair perfectly with their curated wine and cocktail list, setting a flavorful, spirited tone for the crawl.
The next stop is a short, vibrant stroll along Chapel Street, keeping the buzz alive as you transition from Don’s inviting warmth to the playful charm of Better Days Cocktail Bar.
Better Days infuses the crawl with nostalgic energy and creative cocktails, offering a lively playground of board games and retro video games that spark connection and laughter. This spot shifts the vibe into a fun, interactive realm that energizes every social pulse.
The next stop is a quick, buzz-worthy walk down Chapel Street, carrying the infectious energy forward as you head to the polished yet vibrant scene at Blackwoods.
Blackwoods closes out the crawl with a sophisticated yet welcoming vibe, delivering expertly crafted cocktails and a lively atmosphere that invites celebration and connection. It’s the perfect finale for an adventurous night filled with flavor and fun.
The next stop is the end of the crawl, leaving you in the heart of Windsor’s buzzing nightlife scene, ready to carry the night onward or savor the memories made.
This Windsor cocktail bar crawl is your ticket to an electrifying night packed with bold flavors, engaging vibes, and social adventures around every corner. Whether you’re a local or just passing through, let these three standout bars guide your evening from a delicious start to a celebratory finish. Grab your friends, savor every sip, and dive headfirst into Windsor’s dynamic nightlife. Ready to make memories? The night awaits.
Crawl Map