River Medway points along the North Downs, the Weald and Ashdown Forest. The major tributaries are: Minor tributaries include: Former minor tributaries include the Old Bourne River, which flowed through the Brook, Chatham (not to be confused with the main tributary River Bourne). The river and its tributaries flow through largely rural areas, Tonbridge, Maidstone and Medway being the exceptions. The Medway itself initially flows in a west-east direction south of the North Downs; at the confluence of the River Beult, however, it turns north and breaks through the North Downs at the Medway Gap, a steep and narrow valley near Rochester,
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.