The Connecticut River forms Brattleboro's eastern boundary and the state line with New Hampshire. The river valley here is wide and flat, with good walking trails along the Vermont bank. The confluence of Whetstone Brook with the Connecticut, just south of downtown, is the most scenic spot.
The Creamery Covered Bridge, a well-preserved 1879 structure a mile or so upstream, is one of the more photogenic landmarks near town. A network of trails follows the river and the brook through the floodplain forest below downtown — easy walking with occasional views of the water and the New Hampshire hills on the opposite bank. In summer the river is warm enough to swim in at several accessible points.