 However, as there was a gradation between local trails used by few people and more major routes used by many, identifying a point at which the Great Trail begins or ends is an arbitrary matter.The Great Trail system connected with the Overland Trail, which led west, as well as other trails to other parts of the continent.One part of the Great Trail system stretched from Passamaquoddy territory in northernmost New England through the Lakes Region of New Hampshire and down to the Shawmut Peninsula in Massachusetts.