Berlin is a great place, been here for around 3 years and have loved every minute. If your a city person, Conway is the closest place to city life and thats about 45 minutes away. There are a couple bars, but since the mill has closed alot of the population has disappeared. There is a ton of hiking and exploring to do, and the local 4wd club is growing by the minute
(NWOR, North Woods Off Road, you can find them on Myspace and I think Facebook too) and they have a couple spots on Private land to wheel that are cool. Bethel Maine is about 45 minutes away and they have some primo NE wheeling to be run, and the Jeep Jamboree comes every year. The NWOR members are working to get some land opened up in Jerico State Park which is right on the outskirts of Berlin, but that may not happen for another couple years.
As for the winters, they are really nothing horrible. It snows here in October and accumlations start to build around the end of November, early December. The past couple winter have been nothing great, but its not uncommon to have a couple feet of snow on the ground by mid january. the snowmobiling is phenominal from here north, and the town becomes over run during the season with riders. There is skiing nearby and sunday river is right around the corner.
The best part about Berlin is the rent prices. I am paying next to nothing for what would cost me around $1200 anywhere else. There are a few slum lords around to watch for, but you'll know when you pull up and see them driving a van, drinking beer and sporting a Class A mullet.
Overall its not a bad spot and the economy around here seems to be picking up. We have a tractor supply and Walmart to keep you entertained during the spare time! And the Prison sits on some beautiful land so you'll enjoy the view while keeping the peace.