In the mid-1890s, city officials began looking at connecting the new city-owned Emerald Necklace parks with the giant Blue Hills Reservation the state Metropolitan District Commission was putting together just south of the city and the town of Hyde Park.
As the Boston parks commissioners put it in an 1894 report:
This West Roxbury parkway is to be considered as an important chain in a general and intimately connected system of parks and parkways, and it is desirable to make it of a similarly picturesque character as that of the great parkway that runs from the heart of the city to Jamaica pond, by way of the Back Bay Fens and the Riverway. And just as Jamaica park and Leverett park are enlargements in that parkway, so in the parkway to the Blue Hills the Stony Brook reservation would constituted a great enlargement, expanding to the proportions of a considerable stretch of woodland, whose final shape will be perhaps largely determined by the route chosen from the Boston park system.
The Stony Brook Reservation was also a new park the MDC was creating, out of the former Grew Woods, at the Boston/Hyde Park line.
The parks commissioners reported they were looking at three plans for a new parkway through West Roxbury from the Arboretum or Franklin Park to points south.
The most westerly proposal - the route we drive on today - won out, in part because "it is the best as regards scenery," but also because it would open up the surrounding area of "wild woodland and farming land" to development of "fine suburban residences" - and allowed for surface drainage of the surrounding countryside without the need for expensive storm sewers.
The parks commissioners did note one drawback - there was no bridle path from the Arboretum to an existing path along the Arborway that would connect to the new parkway. But the commissioners expressed the hope that Harvard, which, then as now, controlled the Arboretum, would acquiesce to a new horse path through their grounds.
Since Hyde Park was still an independent town (it would not become part of Boston until 1912), the commissioners could go no further with their road than the town line in the middle of the old Grew Woods. But they expressed the hope that the road would be "extended to the picturesque Mother brook, then through the broad, charming landscape of the Neponset-river valley above Hyde Park, then through pleasant fields and hedgerows to the most popular entrance to the Blue Hill reservation."
Today, West Roxbury Parkway (which changes names to Enneking Parkway at Washington Street), intersects at Stony Brook's infamous four-way stop with Turtle Pond Parkway, which heads south to connect with Neponset Valley Parkway (after a brief stretch of River Street), which runs into Milton and along Fowl Meadow - the only part of the Blue Hills Reservation that extends into Boston.