The Dugway is a short (200 foot) street — the right fork of a Y — that was constructed to allow the north end of Main Street to connect to Pine Street without an additional railroad crossing. The name derives from the need to cut through a steep bank in order to make a flat roadway, an improvement suggested by Edward Clark Whiting of the firm of Frederick Law Olmsted in the Olmsted Plan of 1909. In 1931 and before, it was sometimes called North Street. When the railroad tracks were repaired around 2002 for the Adirondack Scenic Railroad, the original continuation of Main Street (the left fork of the Y, to the north, which borders a steep bank dropping down to the Saranac River) was closed and planted with grass. The south side of the Dugway is a steep bank climbing to Prescott House, while the north side is bordered by Triangle Park, the site in 1854 of Saranac Lake's first store and library; Baker's Hotel stood on the east side of Pine Street, between the Saranac River and Stevenson Lane.

It appears that in 1899, Main Street stopped at Front Street, which is shown as connected to Main, though probably only as a "paper street." By 1945 it was marked "impassable" on Sanborn maps, which it probably always had been. It was made passable on foot by the construction of a flight of concrete stairs, which still exist, from the corner of Front Street and Prescott Place down the hill to Main Street, apparently the only such stairs in the village.