As the final weekend before Christmas arrives, Windsor-Essex is buzzing with unconventional and spirited events designed to inject some fun into the festive rush. From bar crawls in hideous knitwear to punk rock renditions of holiday classics, the region offers a perfect escape from last-minute shopping stress.
Festive Bar Crawls with a Twist
Two major bar crawls are set to define the weekend's social scene. The 2nd Annual Ugly Christmas Sweater Bar Crawl kicks off at 7 p.m. on Friday, December 19, in Harrow. Participants are encouraged to don their most outrageous holiday sweaters and visit a circuit of local spots, including the Beerded Dog, Daisy Wine Co., Camoes Portuguese Club, Harrow Legion, and Shine Hospitality.
Meanwhile, Santa suits will be the uniform of choice in Ford City for SantaCon Windsor 2025, starting at noon on Saturday, December 20. This festive takeover invites everyone to hop between popular bars along Drouillard Road, such as Cookiebar, Circuit, Sawyer’s Craft BBQ, and Brown’s Lounge. There's no set route or RSVP required, but attendees can earn a free pint at participating venues by delivering a gift card donation to the Drouillard Place Ontario Early Years Centre at 1102 Drouillard Rd.
Alternative Holiday Entertainment
For those seeking music beyond traditional carols, A Very Merry Warped Xmas offers a punk rock twist on December 20 at The Cherry Rock Lounge (63 Pitt St. E) in downtown Windsor. The event promises a night of high-energy sing-alongs to holiday classics reimagined. Doors open at 9 p.m., with tickets priced at $12 in advance or $15 at the door. A clothing donation will secure a free drink. Tickets are available at showpass.com/warpedxmas4.
Adding to the weekend's vibrant lineup, a drag spectacular in support of Trans Wellness Ontario will take the stage at Walkerville Brewery (525 Argyle Rd.) on December 20. Featuring performances by Xtacy Love, Dallas Ryder, and other local talents, tickets are $20 in advance or $30 at the door, available via transwellness.ca.
More Ways to Celebrate the Season
If a slower pace is needed, Point Pelee National Park (1118 Point Pelee Dr.) hosts a festive morning wellness walk on December 20. This free event includes a stroll on winter trails, gentle stretches, and grounding exercises, culminating with a cozy cup of hot chocolate.
For last-minute shoppers, a holiday market in Amherstburg on Sunday provides a perfect opportunity to find unique gifts. With this diverse mix of events, Windsor-Essex ensures there's something for every taste as the community counts down to Christmas.
