The township was chartered Oct. 12, 1761 by Benning Wentworth, who was the governor of the New Hampshire colony before it became a state in 1788 and before Vermont’s boundaries were established.
The grantees of Maidstone were Connecticut men who never lived in the town. That proved to be an obstacle to settlement because anyone who wanted to purchase land had to go to them for that purpose. Another hindrance was the distance that provisions and other necessities of life had to be transported through the wilderness. At the time of Maidstone’s first settlements, the nearest place where provisions could be procured, grain ground or a horse shod was at Haverhill, N. H., 50 miles down the river. The first gristmill in the area was completed around 1780 by Abner Osgood, but it was subsequently determined that it was in the town of Guildhall. In 1786, another gristmill and a sawmill were built by Ward Bailey at nearby Guildhall Falls, which later became Guildhall Village. Two years later, Maidstone was organized at its first town meeting.
The town became known for its productive agricultural land along the Connecticut River and for its lumber production. The Vermont Historical Gazetteer reported in the 1860s that a single large sawmill on Paul Stream, which runs west to east through the northern part of town, had produced two million feet of lumber each year for transport by rail to Portland, Maine.
South of Paul Stream along the town’s western boundary is pristine Maidstone Lake, a glacially-formed clear, deep, cold lake, measuring about three miles long by one mile wide. The lake and areas around it were designated a state forest and park in 1938. It is Vermont’s most remote state park, offering good fishing for lake trout and salmon, good hunting and secluded hiking trails. Maidstone is rated as one of the top three cleanest lakes in Vermont.