VT 289 begins at a partial interchange with VT 2A in the town of Essex. The route heads eastward through a deep rock cut as it bypasses the village of Essex Junction to the north. After , the rock cut gives way to a mixture of forests and open fields. VT 289 narrows from three to two lanes as it curves southeast to interchange with VT 15. East of VT 15, the highway veers eastward to meet Essex Way, then gradually turns to the south toward the Winooski River as it traverses several small hills.
