Like Ricci's Lane and Allen Street, this was part of the historic cart path known as the old Oxbow Road, first laid out in 1660 to connect Lexington to Watertown and Boston. What was the probably open farmland is now wooded but the stone walls and road bed still remain.
In the late 18th and early 19th century bridges were built across the Charles River allowing for more direct routes to the Boston peninsula, thus the old Oxbow Road became less important as a route to Boston. It did however continue to be one of the main roads between Lexington and Waltham until Waltham Street was laid out sometime between 1830 and 1852. Old Shade Street remained in use as a town road well into the 20th century, even after the construction of Route 2 in the mid 1930s. When Route 2 was rebuilt in the early 1960s the northern part of the street was finally discontinued. Old Shade Street south of Route 2 is still a town street and has four houses, the oldest of which dates to the 1920s. The road was formerly known as Cutler's Lane and forms the westerly boundary of the Cutler farmhouse at 503 Concord Avenue. The Cutler Farm Subdivision at 497 Concord Avenue (corner of Old Shade Street) dates to 2005.