Forget Times Square unless use is part of an integrated program. One of the best, most efficient, ways to inform Fairfield (and parts of Westchester) County about UCONN football is use of the access/egress opportunities presented by Metro-north and Grand Central Station. Every work-day provides a captured and semi-captured group with an outstanding demographic profile.
"750,000 people (including a substantial number of Metro-North users**) pass through Grand Central daily and over 1,000,000 people during the holidays
Metro-North passengers are 55% male and 45% female, the median age is 41. 93% of Grand Central Terminal commuters are college graduates.
Mean household income for Grand Central Terminal commuters is $95,800; 50% of household incomes are over $100,000, and 20% are over $200,000."
Easy to target, more difficult but, not impossible, to create interest.
** My thoughts; not part of demographic info