The Manitoba Challenge is hypothetical, a fantasy. It would be a television show. To understand what it would be like, combine characteristics of these three things:
The Amazing Race, a slick production where teams of people go from place to place to do different challenges, and whichever team achieves this first wins a substantial prize.
A scavenger hunt, which is local, brief, fun, and you provide your own transportation.
A competition involving "A vs. B" games like tennis or chess.

The Manitoba Challenge revolves around a one-day race, with an emphasis on games and puzzles, unlike The Amazing Race. If you want to see the back story / primordial soup / slushpile for The Manitoba Challenge, go here.

Four teams of five (or four) members compete.
Here's where it gets interesting: a treasure hunt does not have to be a linear sequence. A destination can branch off into multiple destinations. Remember that there are teams of five, and this is wired 2014. In practise there are two tracks (sequence of destinations/challenges) for teams to go down at the same time, but with some variations to this model.

I figured first prize would be a treasure chest containing 5,000 loonies, and whatever else looks vaguely like it belongs in a treasure chest. There would be other smaller prizes and trinkets for the winning team, including an envelope with tickets/cards. The second team may get some second-rate prizes, and there may be special prizes for winners of Day One activities - activities which require practise. These prizes could consist of .. well, that sounds like a whole other one of Steve's weird fantasies.

There are Day One activities and Day Two activities a week later. Day Two activities are the race, a.k.a. the treasure hunt.

Day One activities, which don't have to be all in one day, are A vs. B games. There would be three Day One activities. One activity could be big, iconic, charismatic, fun. It could be curling, dragon boat racing, or paintball, but I like the team dynamic of bowling ("Allright Donnie!"). For Special Forces, players could play blind hockey mixed with vision-impaired players.

The Day One activities would give you an advantage. They could affect your start time by ten, twenty minutes. You could also gain intelligence, find out about some Day Two challenges. The most common advantages allow you to try to slow down/hex/curse another team or two. These would be directed at leading teams, with the result being a closer race, unlike the U-turns in The Amazing Race.

Examples of disadvantages are "brainfreeze" during winter, a flat tire that you have to fix for your bike ride (a bicycle built for two!), a hot spice in your otherwise nice Trinidadian food. You might have to do an extra task for one track, like doing laps at the roller rink. Wild goose chases happen, where a clue will send you to two destinations, one of which can't really be found or accomplished (best explained by examples).

Simplifying things a little, the team uses a hex at the time of their choice, informing the race workers that one or two other named teams are to be hexed. Timing matters!

Well, it's my fantasy and I can do what I want. After the Day One activities all teams get together for a meal at a restaurant or other place. This allows the audience to get to know the players. There could be team bonding over the day's activities, there could be another activity, revelations ("You should learn some sign language") and strategizing.
I would even like to see some folk dancing.
The end destination welcoming the winning teams could have its own thing going on. It would be nice if the first to finish in Special Forces could fire a flare gun.

The Manitoba Challenge would have a variety of different types of fun challenges.

Abstract strategy games would play their part in the Manitoba Challenge. They would nicely belong in the Day One activities, and you could also have a challenge where, e.g. you can't get your next clue until your king escapes when you keep playing Tablut against a neutral person.

Here are the themed versions of The Manitoba Challenge:

Fun in the Sun - Think volleyball
Cabin Fever - Think curling, skating down the river, and crokinole with some hot chocolate
Trick or Treat - Devilish, fear factor and trickery
Bison Challenge - Meet people in the community
Friday Night - Think bowling, darts at the pub, poker, karaoke, movie trivia in a hot tub.
Special Forces - Think boot camp. You're in the army now.

The geographic angle is tempting but tricky.
Dragon Challenge - The East Asian cultures. Think dragon boat, Go.
Cherry Blossom Challenge? - Go, origami, karaoke, karate. Now do you see where folk dancing fits in? Some interesting prizes.

And there's the mysterious Cobra Gold.