Since I live in the area, I end up downtown Hartford for a drink or dinner. For the past few months, with the college crowd gone, the Downtown area has been pretty desolate. People are spending less money on going out, and more nights home. If you take a ride to Manhattan, you might not see this as much as you see it in Hartford.
Every restaurant I go to downtown has a minimal crowd. When school starts again, Thursday nights and weekend nights will be bring a flood of college students to Ann St. and Main St. But until then, these quiet nights are nearly unbearable and boring. The best thing to do is to spread the word about good places to eat and drink downtown, because there are a lot of great places that also offer really good deals. It's not the food so much that will set you back, but the drinks. At least parking on the street isn't a huge problem this time of the year.