New England Explorer begins in Williamstown, Massachusetts where Overland is based. Located in the northwest corner of the state, Williamstown is 3 hours north of New York and 3 hours west of Boston. Students are either dropped off in Williamstown or fly into Albany International Airport just over the border in New York and are shuttled by Overland the 42 miles to Williamstown. After hiking in the Berkshires, groups travel by van to hike the Green Mountains of Vermont and the White Mountains of New Hampshire. The trip ends with sea-kayaking off the coast of Maine and a final celebration back in Williamstown.