Nice items! I am not a hockey collector, but as a Canuck, quite a few hockey items have passed through my hands.
The letter, if real (I can't offer any opinion on the sig) should bring a nice payday. Is the content interesting (hockey related)?
Here are a couple of links to Lord Stanley letters/docs from a popular auction house near Montreal that specializes in hockey items.
https://www.classicauctions.net/LotD...ntoryid=123547
https://www.classicauctions.net/LotD...ntoryid=122222
https://www.classicauctions.net/LotD...ntoryid=116178
The Winter Carnival programme and medallion, I have never seen before and while interesting, aren't specifically hockey related (unless I have missed something in the interior of the program).