There are a number of things that keep me from viewing our games against UMass as warranting a trophy.
For openers, we've been playing them since the 1890's yet prior to this fall there was never any desire anywhere of this being a trophy game. If the winner should have received a trophy, one would have materialized before the great depression.
That we now have a series of games with them is far more the result of need for both parties (until UMass starts play in the MAC next year) than any connection between the schools, which given the proximity and history is an indictment on the idea of this being a rivalry. The only reason this is above the other New England flagships, who were also long time Yankee Conference foes is because UMass is the only one of them who upgraded football.
I know that some have brought up some silly, long standing trophies that other schools compete for (little brown jug was brought up, old oaken bucket was not but is a similar deal), but those have been around from before WWII and some incident led to its creation. Basically UMass' collective tried to ConnFlict us, just as nutty Bob Diaco tried to ConnFlict UCF. There needs to be some natural development of something for the trophy to not be lame as hell. There wasn't in either case where someone tried to create a trophy.