It begins in the Green Mountains , and flows through the counties of Rutland County and Windsor County , flowing into the Connecticut River in the town of Hartland . The Ottauquechee rises in the Green Mountains in eastern Rutland County in the town of Killington , and flows generally eastwardly into Windsor County , where it passes through or along the boundaries of the towns of Bridgewater , Woodstock , Pomfret , Hartford and Hartland ; and the villages of Woodstock and Quechee . It joins the Connecticut River in the town of Hartland , about 4 miles ( 6 km ) south-southwest of White River Junction .