The wilder in portsmouth or the Wallingford dram in Kittery have the best cocktails. I'm pretty sure they're owned by the same people.

For things to do there is ice skating at strawberry banke, maybe live music at the press room, karaoke at Daniel's street, pool and darts at legends. The music hall might have something good going on. I'd check some local events websites and look around. There's always something going on. Just last weekend there was a great steely dan cover band in Kittery so who knows