Here are some Reeactment Societies that do WW II. There are other Reenactment Societies that do other periods; War of 1812, Civil War, WW I, etc.
5th Canadian Armoured Division Signals
1309 Sunbury Rd.
RR#2 Inverary, ON., K0H 1X0
8 Section, 5 Provost Coy, 5 Cdn Armd Div
17217 -1435 Prince of Wales
Ottawa, ON., K2C 1N5
Contact John Cameron, 613 225 9522
provostsgt@yahoo.com
The Perth Regiment, 11 Cdn Inf Bde, 5 Cdn Armd Div
85 Fog Rd.
King City, ON., L7B 1A3
Contact Gavin K. Watt
The Perth Regiment
P.O. Box 99628
1097 O'Connor Dr.
Toronto, ON., M4B 3M
Contact: Capt R.D. Lawrence
416 250 3341
1st Canadian Parachute Bn, HQ Coy. 3rd Br Para Bde, 6th AB Div
4358 Majestic Lane
Fairfax, VA USA 22033
Contact: Glenn Kimmell
703 263 9596
There is another that covers various periods:
Upper Canada Volunteer regiments Organisation
RR #1
Orillia, ON., L3V 6H1
Contact: Roger Holliday
705 326 0709