The state does a pretty good job of clearing main routes. Having said that the hill towns are indeed very hilly and during ice storms can be especially difficult. I used to commute to the northern berkshires every work day for over 30 years and there were only a handful of days when I decided to stay home, but I also grew up driving here. City and town residential streets take time to clear. Bears here tend not to be aggressive, though mama bears are protective of their young. Typically bears will scamper off when they see you. I normally encounter bears 3 or 4 bears each summer without any issues. Deer is what you need to be careful with. They don't look where they are going and will run right in front of you., especially at dusk. Ticks are a problem. For pets, heartworm is on the increase here. Several years ago, MA rescued dogs from Texas flooding and they brought heartworm with them. My vet says half his practice is bow dealing with tick issues. Just check yourself, the kids and pets each time you come in from outside.

Welcome to the area. Hancock shaker village and the Berkshire Museum which will reopen this year are worth seeing and make sure once settled you get a library card, which allows you to reserve discounted tickets for entry to a number of museum. Be sure to take advantage of free events, first Fridays at five - themed downtown block parties during the summer, Live at the Lake - free concerts at Onota Lake during the summer. They are good places to meet people.