Coming from a WPI (Worcester Polytechnic Institute) student I can tell you that the drivers are particularly bad in Worcester. On that note though the riding is pretty easy as others have noted if you can put up with horrendous drivers in the area. The problem is that so few people bike in Worcester, cars dont understand the basic etiquette of sharing the road and as such will give you no passing room or they will act aggressively towards you.

Also, yes get some good studded tires or get comfortable with snow riding because when it snows in Worcester IT SNOWS. This past year we were so inundated with the stuff that no biking was even possible for me, so be prepared to either have superb winter gear, or have a back-up plan.

Also on the note of "Where to live". You want anything North of Park Ave, basically. South of Park ave is not so good.