 It later passed through Manchester Green, where the post road became reconnected with Route 6, and, for the first time, U.S. Route 44.Just before leaving Manchester and entering Bolton, the post road breaks off Route 44 onto Middle Turnpike East (the portion of Route 44 between Manchester and Bolton is known as "New Bolton Road")

Bolton serves a unique role in the post road, as it was the border between the flat and tranquil Connecticut River Valley, and the hilly and turbulent Eastern Upper Highlands.Entering Bolton on Middle Turnpike East, the traveler encountered a fork and could choose to head southeast on Bolton Center Street (later Center Street) to the settlement of Bolton, or stay on Middle Turnpike East to reconnect with Route 44 and head east on the original Mohegan Indian Trail through Bolton Notch, a natural depression in the ridge that dramatically sped up transit and served as a demarcation between the two geologic landscapes.