I spoke with a number of officers and some people from the traffic division. There was no clear cut answer to my questions. However I can tell you that they did clear up one item for me. Since a pocketbike can NOT be registered, they can not charge you with driving an unlicensed vehicle.
Saying that, you're a bit better off. But here's the bad news.
Quote:
Operation of off-road vehicles on highways
Certain operations prohibited
32(1) No person shall operate an off-road vehicle
(a) on privately owned land without the express or implied consent of the owner or lawful occupier of the property;
(b) on Crown land allocated by lease or permit, without the express or implied consent of the lawful occupier of the property, unless the operator is otherwise lawfully authorized to enter such land;
(c) within 30 m of a dwelling between the hours of twelve midnight and seven o'clock in the morning, unless the dwelling is located on the operator's own property or property under the operator's control or as an invited guest; or
(d) within 30 m of a playground, or area set aside for other recreational use, unless the area is enclosed or fenced or unless the off-road vehicle is required for the maintenance or operation thereof.
Operation in parking lots
32(2) No person shall operate an off-road vehicle in a parking lot unless it is used to gain access
(a) to or from an off-road vehicle use area; or
(b) to the vehicle used to transport the off-road vehicle to an off-road vehicle use area.
33(1) Except as may be authorized under another provision of this Act or under the regulations, no person shall operate an off-road vehicle
(a) upon or across a roadway or the shoulder thereof;
(b) on or across the median of a divided highway;
(c) on the right-of-way of an interchange; or
(d) on or across a sidewalk.
General offences and penalties
67(1) A person who contravenes a provision of this Act or the regulations, or of a by-law passed under the authority of this Act, for which a penalty is not otherwise provided is guilty of an offence and is liable on summary conviction to a fine of not more than $2,000.
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This quote is from the Off Road Vehicles Act of Manitoba. Essentially it says no off road vehicle (trike, quad, snowmobile, mini-bike, dirt-bike, trail-bike etc) which would include pocketbikes, can travel on streets, highways or sidewalks. If you are caught doing this there can be a fine of up to $2000.
Of course you should also be aware that riding on crown land or private property can also get you charged with tresspassing.
Quote:
Trespassing offence
1(1) Subject to subsections (2), (3), (4) and (5), any person
(a) who unlawfully enters or in any way trespasses upon lands or premises that are the property of another and are wholly enclosed; or
(b) who enters or in any way trespasses upon lands or premises that are the property of another and are not wholly enclosed, after being requested by the owner, tenant or occupier not to do so, or who, having entered the lands or premises or committed the trespass, refuses to leave upon being requested by the owner, tenant or occupier to do so;
is guilty of an offence, whether or not any damage has been occasioned by the entry or trespass, and is liable on summary conviction to a fine of not more than $5,000.
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It's not worth it, don't take your chances riding on the streets!