I haven't seen all the shows, so hopefully I'm not duplicating. With the holiday season approaching, a port wine or other dessert wine show would be interesting. A warm beverage show for winter. Hard cider is growing support. What about snack food like pretzels, chips and what not.
I find Tawny port to be a nice compliment but in general I prefer non alcoholic drinks. With that in mind, I'd recommend cream soda. My outside the box suggestion would be white cherry Gatorade...surprisingly good with cigars.
I hadn't had Port in years. It was the stage between red wine and brown liquor. Port was always good with chocolate or walnuts so it should pair easily.
With the cold weather hitting Canada, how about a hot toddy, hot cocoa, or spiced cider so Surgeon doesn't freeze?