TL;WR
What to do.
Get crafty tonight at Descendants Beer & Beverage with Beers & Boards. Get into the Halloween spirit with some fun, scary and funny Halloween signs. Starting at only $45, registration includes all materials and hardware needed to complete your Halloween sign and a $5 voucher to enjoy a delicious snack or non-alcoholic drink. Tonight, Monday, Oct. 16 at 6:30 PM.
Rhapsody Barrel Bar has their Blackball Comedy Night this Tuesday, Oct. 17 starting at 8:30 PM. It's free comedy in downtown Kitchener.
Demetri Martin's "Lets Get Awkward Tour" hits the Centre in the Square this Thursday, Oct. 19 at 7:30 PM.
Open Sesame brings awesome live music to downtown Kitchener with Bogues (Nashville, TN), Grizzly Waves (BC), Castlefield (Ottawa) and more special guests. Full details here. Friday, Oct. 20 starting at 7 PM.
(Editor's note: I just copied this word for word from their site because it's amazing) This Friday, Oct. 20, 2017, join THEMUSEUM, Nerd Nite Kitchener Waterloo and Cult KW for a slammin' night of nostalgia from back in the day - because we all know the 90's was all that and bag of chips! Dance Mix 90's - featuring: pimpin' trivia, phat DJ hits & dancing, bangin' 90's throwback activities, mad video games, food & drink (DUH), and a sweet prize for the most totally 90's outfit.
The Walper Hotel presents Taps & Apps in support of Big Brothers Big Sisters of Waterloo Region on Thursday, Oct. 19. I had to check twice, because I saw apps and thought it was a hackathon - but "apps" refers to appetizers and now I wonder if I'm too deep into the tech scene. BUT ANYWAY - your favourite local restaurants, breweries, live music and fun times all for a great cause at one of the region's most distinctive landmarks--the Walper Hotel. Admission includes access to the event, 10 food samples and 10 drink samples donated by their generous partners.
The 17th annual Rainbow Reels Queer and Trans Film Festival runs from Oct. 19-22, 2017 at the Princess Cinema in uptown Waterloo. The festival brings you film, art, comedy, workshops, parties and community.
The 3rd annual Kitchener Public Library DIY Festival is here to answer the age-old question “what should I do for fun (or money)”? KPL will be hosting all kinds of amazing local creatives to help you discover your new hobby or business. It's all free, for all ages, and interests. Saturday, Oct. 21 from 1 PM to 4 PM.
Where to be for...
...Music.

Birds of Bellwoods & The Pick Brothers Band
Wed., Oct. 18 | 7:30 PM
Maxwell's Concert & Events
...Talk.

Creativity: A Public Health Issue with Margaret Martin and Joan Sanger
Wed., Oct. 18 | 7:00 PM
THEMUSEUM
...Movie.

3 Dead Trick or Treaters & Prince of Darkness
Thurs., Oct. 19 | 6:45 PM
Apollo Cinema