In my experience, it's very possible to meet people through smaller restaurants/bars

If you want to start out small, there's a nice bar / restaurant that has a very nice clientele. Blue Orchid. It's a bit unknown but it's a bit easier to make friends since its not very crowded and you'll run into the same people over and over. The owners are also very nice and friendly and really make you feel at home. They also have the best happy hour in New Haven that I know of Fri/Sat 10 to close. LGTB friendly as well.

BAR as well but it gets hard to have a conversation if it gets packed

Bumble also has a friend feature as well.

I'd say that making the first new friend outside your existing circle is usually the hardest, but once you know one of two people it gets easier since they can introduce you to more people. So don't get discouraged, it's possible :)