Goldthwait's views were generally those of a loyalist, feeling that despite the grievances of the colonists, a break with England would be a mistake. After the Battle of Lexington and Concord started the Revolutionary War, the Massachusetts militia laid siege to Boston, trapping the British Army and the citizens of the city inside. When the Royal Navy evacuated the British Army 11 months later, it took thousands of loyalists with it to Halifax, Nova Scotia. Goldthwait, though, decided to stay in Boston. However, he was not condemned as a loyalist, and his valuable properties in Boston and country estate in Roxbury, Massachusetts were not seized by the revolutionary government.