By BRUCE HAULMAN and TERRY DONNELLY

Quartermaster Drive was completed between what is now Monument Road and Portage in 1914. Before then, the road to Portage followed present-day SW 216th Street and dropped down to Portage at Tramp Harbor, where Highland Avenue SW is today.

Portage was first filled in 1897 when a crew from the Dockton Dry Dock built a causeway to allow a water-level passage for those going to Dockton. In 1914, King County constructed the bulkhead along the northwest end of Quartermaster Harbor and laid the road seen in the 1914 photograph.

Notable in the photograph is the Sherman House where the road turns, which remained there until it was burned in 1936. The house at the top of the hill in the center of the photograph is no longer there. The house along the water, to the left of the road as it sweeps up the hill, was built by Dick Fredrickberg around 1912.

On the left-hand side of the 1914 photo, on the beach lies the remains of the Molly Bleeker, the large flat-bottomed barge that served as a home for the Bleeker family and used to transport bricks from their brickyard at Burton to destinations around Puget Sound. The area on the point above the remains of the Molly Bleeker was declared Bleekerville, but was never developed, much like many similar plots around the islands that remain undeveloped.

The current photograph shows the road as it exists in 2010. The original bulkhead lies about where the fog line of the current road is, and the road itself has been significantly widened. A new rip-rap bulkhead has also been installed by King County.

The Sherman House is gone and is now part of the Middling property. The house at the top of the hill in the original photograph was taken down and replaced by the current house that is obscured by the trees. The Frederickberg house along the water is still there, although substantially remodeled and expanded. Additional houses have been built on the hill above where the Molly Bleeker was beached, and additional waterfront homes have been built.

The construction of this waterfront road to Portage increased the demand from Dockton for a waterfront road to connect them with Portage. In 1924, King County completed a road with a bridge across Rabb’s Lagoon that connected to Dockton.

— Terry Donnelly is a landscape photographer. Bruce Haulman is an island historian.