Route 109 is a state highway in eastern Massachusetts. It runs from Route 16 in Milford east to the VFW Parkway in Boston. Most of Route 109 runs along a portion of the Hartford and Dedham Turnpike. Route description Route 109 begins at Route 16 in Milford, just east of Route 85's southern terminus. The route proceeds to the east, meeting Interstate 495 (I-495) at exit 19 before crossing into Norfolk County and the town of Medway. Route 109 passes through northern Medway, crossing Route 126 along the way before turning onto Main Street. The highway continues into Millis, where it crosses Route 115 in the center of town. The road then crosses the Charles River as it enters Medfield, passing through the center of town where it intersects Route 27. East of Medfield, Route 109 travels along the Dover–Walpole town line before entering Westwood. The highway passes through the town, easing towards the urban landscape of metro Boston. North of the center of town, Route 109 intersects I-95/Route 128 at exit 31 (old exit 16) as it enters Dedham. Route 109 passes through northwest Dedham, crossing the Charles twice more before crossing into the Boston neighborhood of West Roxbury, where it immediately meets the VFW Parkway and ends. The VFW Parkway, which has its southern terminus at the intersection with Route 109, formerly carried U.S. Route 1 (US 1) into the city, before US 1 was rerouted along I-95 and I-93 through Braintree and downtown Boston, due to the cancellation of I-95 in Boston during the 1970s. As such, Route 109 no longer ends at a numbered highway, although the Boston-Providence Turnpike runs south from this intersection to join the current US 1 at its interchange with I-95/Route 128. South of the interchange, US 1 runs along the Turnpike. History The Hartford and Dedham Turnpike was chartered on March 9, 1804, to close a gap in the turnpikes that were being built to replace the Middle Post Road between Dedham and Hartford. It ran from Dedham southwest to West Medway, where it continued as the earlier Ninth Massachusetts Turnpike and Boston Turnpike to Hartford, Connecticut. North of Dedham, the Norfolk and Bristol Turnpike continued to Boston. The turnpike, built in 1807, was never a success. In 1821 it was closed to all but local travel due to its condition; it became a free road in 1830, with the rest