TL;WR

What to do.
Looking for some comedy on a cold December Monday? Abe Erb Kitchener has Dom Pare on stage at 8 pm tonight, Monday Dec. 18.
The Princess Cinema presents their 32 annual showing of "It's A Wonderful Life". Admission is free with a donation to the Food Bank of Waterloo Region. This Tuesday, Dec. 19 at 7:30 pm.
Why watch it on someone's Instagram stories when you can witness Santa Claus in real life at Becky's Apartment this Wednesday, Dec. 20. Santa and Becky are raising money for the food bank. Does it show that I'm not in Becky's demographic because I spell out "apartment"?
If you're trying to fill up those stockings, the folks at Descendants Beer & Beverage have you covered this week. From Monday, Dec. 18 to Saturday, Dec. 23, they have Last-Minute Maker Markets running from noon till 6 pm each day.
Grab your best ugly Christmas garb and get into to the festive spirit with the Dan Howler Band as they present "Merry Christmas, Ya Filthy Animal". This Friday, Dec. 22 starting at 9 pm.
The Rusty Nail Comedy Annual Xmas Show is on Friday, Dec. 22 starting at 8 pm. This year's show features Tom O'Donnell (Russell Peters tour, Rude Dudes podcast) and Courtney Gilmour this years Just For Laughs homegrown winner - plus two Rusty Nail Comedy Fan favourites - Tige Wright (Big Easy Comedy, Jeff Lesson comedy record taping) and Jason Allen (Yuk yuk's, Cottage Country comedyfest, Go Yuk yourself winner).
Descendants Beer & Beverage has Jesse Webber (from The Guilty Pleasure Band and more) on stage this Friday, Dec. 22 starting at 8 pm.
No one's judging you if you're still shopping on Saturday, Dec. 23. Well, as long as no one recognizes you. Wear a disguise and head to the Kitchener Market from 7 am to 2 pm for their last-minute Christmas market.
Brew Donkey tours presents A Grand Ride (North) this Saturday, Dec. 23 from 10:30 am to 3:15 pm. The tour takes you to Block Three, Murphy's Law Distillery, Elora Brewing Co and Innocente Brewing.

Our friends at Astrodog Media have a holiday contents for swag, bragging rights and glory (and also a major grand prize) with Ruff Galaxy.
Play each week to win prizes like toques, tees and hats. The top ten high scorers will win admission to RUFF GALAXY: Unleashed, an in-person tournament held in January 2018, where each entrant is competing to win $10,000.00 (CAD) of in-kind video production services provided by Astrodog Media.
Where to be for...
...Music

Celtic Christmas with the Gaes
Fri., Dec. 22
Churchill Arms
...Trivia

Harry Potter Trivia
Thurs. Dec. 21 | 7 pm
Watchtower Restaurant
...Movie

TV Christmas Special Compilation Party!
Thurs. Dec. 21 | 6 pm
Apollo Cinema