10) Dover, Massachusetts
Dover is only 15 miles from Boston and sits on the Charles River. It was first settled in 1640, but didn’t become the town of Dover until 1836. Boston Magazine has ranked the schools as being the best in the state three times, in 2013, 2014 and 2015. The median household income is $187,829, more than two and a half times the state median. The median home price is around $1 million and the population is 6,279. The town maintains miles of trails for walking, horseback riding and cross-country skiing. Residents have access to a boat landing, fishing and ice skating on Channing Pond. Caryl Park’s 83-acres of land offers tennis courts, lacrosse and soccer fields and walking trails. Locals also enjoy the annual 5k and Dover Days Festival.