There's a Kitchener-Waterloo Crypto Interest Group, with a Wiki and a Mailing List.

The University of Waterloo Computer Science Club is hosting what looks to be a great series of lectures on Security and Privacy:

Held in MC 4041, on 2013-10-08, at 5:00PM.
The first lecture of our security and privacy series. By PhD student Sarah Harvey.
http://csclub.uwaterloo.ca/events/MC_4041-2013-10-08-5:00PM

Held in MC 4060, on 2013-10-15, at 5:00PM.
The second lecture of our security and privacy series. By undergraduate student Eric Dong.
http://csclub.uwaterloo.ca/events/MC_4060-2013-10-15-5:00PM

Held in DC 1302, on 2013-10-24, at 6:30PM.
The third lecture of our security and privacy series. By undergraduate student Simon Gladstone.
http://csclub.uwaterloo.ca/events/DC_1302-2013-10-24-6:30PM

Held in MC 3001 (Comfy), on 2013-11-05, at 6:00pm
The fourth event in our security and privacy series. By undergraduate students Murphy Berzish and Nick Guenther.
http://csclub.uwaterloo.ca/events/MC_3001_%28Comfy%29-2013-11-05-6:00PM

Held in MC 4060, on 2013-11-12, at 5:00PM.
The fifth lecture of our security and privacy series. By MMath alumnus Zak Blacher.
http://csclub.uwaterloo.ca/events/MC_4060-2013-11-12-5:00PM

• KWLUG - Encrypting E-mail with GnuPG, Thunderbird and Enigmail (2013-12-02)

• KWLUG: Why You Should Care About Security and Privacy
  Sarah Harvey repeats her lecture on how much we need to be concerned about the security and privacy of our information.

• KWLUG: Informal keysigning at the KWLUG meeting

• Informal keysigning at the KWLUG Meeting

• KWLUG: TOR: The Onion Router

• Kwartzlab: Cryptography Workshop