Trinity is the only really urban NESCAC liberal arts college (Tufts is NESCAC and urban, but not a LAC). In theory, this could be an attractive market niche; many large cities are significantly safer and more attractive than they were a generation ago, and today’s students seem to have a lot more interest in attending urban schools. The problem, though, is that Hartford has lagged behind many other cities in terms of revitalization or gentrification. If Hartford ever gets safer and hipper, like maybe Providence or Hoboken, then interest in Trinity would probably soar.
One thing that puts Trinity at a general disadvantage, relative to other NESCACs, is its endowment. The Trinity endowment is around $500 million, which is certainly respectable. But it’s on the low side for NESCAC; most other NESCACs are in the $1 billion to $2.5 billion range.