I bought most of these pins on my business trips. Worked under contract with many US companies. Design heavy industrial buildings, Bridges, Nuclear.  During these trips (1974-2000) I collected a fair amount of pins from all over USA.   

    1.     Tourist tent
2.     Republican 2008
3.     I.E.S.I  Champs. 
4.     S S Ski resort
5.     Where, when, and why I bought this badge? No clue. But this devil is very funny.
6.    Princess Cruise pin
7.     TCI, 1985
8.     9. Alaska, Flag; Elk  What a State! 3 times cruise. 3 times job contract in Anchorage. One time driving from Las Vegas, 2012 (Total 11,000 miles)    

    10. Flag USA
11. Spirit of Communication
12. Where, when, and why I bought this badge I do not know.
13. City Club. Where, when, and why I bought this badge I do not know. 
14. Canadian Ice cream badge. I clearly remember that shop. 1988 y. I was diving from Florida to Oregon (Story what happened in Winnipeg, per your request) and bought this badge in ??? From signature on the back of the badge, I can't get the name of that Ice Cream parlor shop. Is anybody can help?
15. Blood donor.
16. Dura Tractor
17. NY Stock Exchange
18. Monterey, CA. 2002 New year celebration.
19. Portland Rose Festival. 1975 y.
20. Go Perot. 1992 y. Ross Perot Pin Back Presidential Campaign Button Badge

     21. Fashion badge

22. Juror, 1992. Allentown, PA  
23. International ... Machinists ... Aerospace...
24. Portland Rose Festival. 1975 y.

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