Heroes Hockey Challenge will be featured in five cities: Vancouver, Edmonton, Toronto, Montreal, and Halifax. The cities were chosen given their size and proximity to major military bases or strong connections to the Canadian Forces and the NHL.

In each city, Heroes Hockey Challenge will hold a charity Gala Dinner with the formality and ceremony of traditional military dinners. Participants will dine with serving members of the Canadian Forces (Afghanistan veterans, where possible) and NHL stars at each table. The Gala Dinner event will also include celebrity appearances, VIPs from the Canadian Forces (serving and retired), celebrity MC and guest speakers, special entertainment, military bands, and pipes and drums. Extensive media coverage will be leveraged throughout. Fundraising activities will include live and silent auctions.

Following the Gala Dinner, in each city, Heroes Hockey Challenge will schedule a hockey game between the NHL Alumni and soldiers from the Canadian Forces. All games will be in the main venues used by the NHL. NHL alumni will be in the traditional old style jerseys and the military teams will be in specially designed "desert cam" based jerseys.

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