There are several smaller towns bordering Worcester -- Grafton and Auburn come to mind -- fewer hills to deal with. A car would be required; services (snow removal) might be better; housing in this entire area is expensive; and you wouldn't be in Worcester proper. Get into Worcester often -- pick a pub or two, become a regular, bartenders are a great source of info. Volunteer at one of the numerous charities that interest you and there are plenty of churches if you like. You'll make friends -- like anyplace else, you have to put yourself out there. Winter can be a challange -- dress for it --learn to ice skate -- embrace the snow & cold. Spring and Fall are terrific in New England.