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Each December, as Windsor begins to glow with tinsel, lights, and the hum of Christmas crowds, another tradition quietly returns to the local calendar, one that’s a little louder, a little redder, and undeniably festive. The Windsor Santa Pub Crawl, now more than a decade old, has grown from a casual social outing into one of the region’s most anticipated holiday-season events.
Dressed head to toe in Santa suits, elves’ ears, or whatever festive creation they can dream up, participants take to pubs and bars across the Hawkesbury for a night of celebration that’s equal parts merriment, community spirit, and local camaraderie. These sentiments are echoed by long-time Santa Pub Crawler Troy Myers.
“Great to catch up with old friends and a great atmosphere,” Myers said.
While the format mirrors a global trend of holiday-themed pub crawls, Windsor’s version has developed a distinctly local character, shaped by its people and its pubs.
A Tradition With Deep Local Roots
“Yes, it’s that time again, Santas, for our 14th Windsor Santa Pub Crawl. Time to dust off the outfits and get your drinking boots on. We’re looking forward to seeing familiar and new faces this year to help us support Hawkesbury Helping Hands and celebrate this festive time of year,” organisers said.
What began as a fun seasonal get-together has steadily become woven into the Hawkesbury’s festive fabric.
Though always promoted as a light-hearted celebration, the crawl often doubles as a fundraiser in true Hawkesbury fashion. Organisers and attendees have supported local charities and community groups over the years, blending fun with a strong sense of purpose. The tradition now reflects a community that shows up not only to celebrate but to give back.
“We organise the Windsor Santa Pub Crawl because Christmas is a time for friends, family, and community to come together. It’s a chance to celebrate, be grateful for what we have, and recognise that many in our community aren’t as fortunate,” event organiser Matthew Cotter said.
The night has even become known for its unexpected Christmas magic, with stories of couples meeting under the mistletoe and love lasting well beyond the event.
“Over the years, we’ve even seen people find love on the crawl. There are now couples, marriages, and even kids who can trace their story back to meeting in a Santa suit on this night,” Cotter said.
The 2025 event is scheduled for Friday, 19 December, kicking off mid-afternoon at 3.30 pm at the Windsor Bowlo. As always, details first appeared on Facebook, where the crawl is primarily organised.
A Night of Festive Fun and Fundraising
What began fourteen years ago as an informal gathering of ten friends has grown into a quirky, joyful, and much-loved part of the Hawkesbury’s Christmas season. Whether you join for the drinks, the costumes, or simply the company, the Windsor Santa Pub Crawl continues to celebrate what the Hawkesbury does best: community, connection, and a great night out raising money for Helping Hands.
“If you want to be part of something bigger than yourself, a community of people who care, give back, and have a great time doing it, this is the event. Bring your friends, bring your family, or come on your own and meet new people. Everyone is welcome — it’s not just for drinkers,” Cotter said.
Whether you’re looking for love, hoping to meet new mates, or simply wanting to end the year on a festive high, the Windsor Santa Pub Crawl offers a night where everyone is welcome and the Christmas spirit truly comes to life.
Click the link below for all the pub crawl details
