Maidstone is six miles downstream from where the River Medway, having flowed in a generally west-east direction, is joined by the Rivers Teise and Beult at Yalding and changes its course to a northerly one. It cuts through the ridge formed by the greensand, so that the town occupies a site on two opposite hills, the easterly one containing the town centre. Beyond that, and higher, is Penenden Heath. The River Len joins the Medway at Maidstone. Though a short river, it provided the water to drive numerous watermills. The Loose Stream, which rises at Langley and joins at Tovil, once
Maidstone, Vermont the southwest, Ferdinand to the northwest, and Brunswick to the north, all in Vermont. Across the Connecticut River are the New Hampshire towns of Stratford to the northeast and Northumberland to the east. The only crossing of the Connecticut River from Maidstone is the Janice Peaslee Bridge in the northern part of town, leading to Stratford village. Vermont Route 102 travels the length of the east side of town, staying in the Connecticut River valley. According to the United States Census Bureau, the town has a total area of , of which is land and , or 5.39%, is water.