đź“… Open Today: Crawl likely open on Fridays
Discover Windsor’s coolest cocktail bars on this lively crawl through three unique venues: Three Monkeys, Better Days Cocktail Bar, and Blackwoods Wine & Cocktail Bar. Nestled in a snug, quirky neighbourhood, these spots are perfect for relaxing with expertly crafted drinks, whether you’re into classic cocktails or innovative mixes. Plus, enjoy DJ parties on weekends that keep the party going. Perfect for a fun, memorable night out with friends!
Last updated: July 2025
Dive into an electrifying night on Windsor’s iconic Chapel Street with this cocktail bar crawl designed for thrill-seekers and cocktail aficionados alike. Start by soaking in the energetic and intimate atmosphere of Three Monkeys, where lively weekend DJs set the tone for a night of social buzz. Then, ramp up the fun at Better Days Cocktail Bar, a playful hotspot where nostalgia meets creative mixology and games spark contagious laughter. Finally, cap off the crawl at Blackwoods Wine & Cocktail Bar, where the vibe shifts to stylish sophistication without losing the vibrant buzz—making it the perfect place to toast to new friendships and unforgettable memories. This crawl masterfully blends playful energy with crafted elegance, taking you on a seamless adventure through Windsor’s cocktail scene.
Launching the night at Three Monkeys sets an upbeat and intimate tone with its quirky charm and weekend DJ energy, making it the perfect social spark to ignite the crawl.
The next stop is a brief, lively stroll down Chapel Street, keeping the energy high as you move to a spot known for playful fun and inventive cocktails.
Better Days amps up the adventure with its nostalgic gaming vibe and creative drinks, creating a vibrant playground for laughter and connection mid-crawl.
The next stop is a quick walk along Chapel Street, easing you into a sophisticated yet lively atmosphere to elevate the night’s finale.
Ending the crawl at Blackwoods offers a refined yet spirited setting where expertly crafted cocktails and a curated wine list provide an elegant crescendo to your Windsor night out.
The next stop is the conclusion of the crawl, just steps away, allowing you to savor the last sips without missing a beat.
This Windsor cocktail crawl is your passport to an unforgettable night where each bar unlocks a new chapter of excitement, flavor, and social connection. Whether you’re chasing energetic beats, nostalgic fun, or polished sophistication, this route delivers a seamless and spirited adventure. Ready to explore Windsor’s vibrant cocktail culture? Gather your crew, map your course, and let the night unfold one lively stop at a time.
Crawl Map