safewise 2/1/16: The 20 Safest Cities in Massachusetts — 2016. Wayland, our safest Massachusetts city, has claimed the top spot for the second year in a row. This proud community is a modern-day melting pot that represents the best of America’s values: the community’s philanthropic spirit actively fosters volunteerism and civic responsibility. Wayland lives up to its ideals with a safety record boasting fewer than 20 total reported crimes, an impressive number for a city of more than 13,000 residents.