Following the enactment of authorizing legislation in 1894, the Metropolitan Parks Commission (predecessor to the Metropolitan District Commission (MDC) and today's Massachusetts Department of Conservation and Recreation (DCR)) began working with Charles Eliot to plan a parkway to provide access from Boston to the Middlesex Fells Reservation.

The plan that the commission and Eliot finally drafted called for an arterial trunk (The Fellsway), which would run north through Medford and Malden, and then split into two branches.

Fellsway West would provide access to the promontory point at Pine Hill in Medford (now visible on the west side of Interstate 93) and the western parts of the reservation, while Fellsway East would provide access to Bear's Den Hill in Malden, and points east.

These corridors were wide (120-foot (37 m)) rights of way, in order to provide for several modes of transportation: automobile, street car, and pedestrians and cyclists.

The Medford and Malden portions of The Fellsway, including its medians and Wellington Circle, are part of the National Register listing for the Fells Connector Parkways.

The road runs west from the northern end of The Fellsway, soon after crossing Massachusetts Route 60 just across the Malden-Medford line in Medford.

The oldest portion runs to East Border Road at the southern edge of the Fells, crossing Massachusetts Route 60 and passing Fellsmere Park.

It then becomes a border road, skirting the eastern edge of the reservation in Melrose before reaching its end at a junction with Pond Street and Lynn Fells Parkway in Stoneham.