Middle Road begins at Main Road (NY 25) in Greenport. It runs west to Southold as a two-lane undivided road.

Photos taken August 2009.

In Southold, Middle Road widens to become a four-lane divided road. It continues west to Mattituck.

Photos taken August 2009.

Turn left onto Wickham Avenue at this traffic light for a crossover to Main Road (NY 25).

Photo taken August 2009.

At the western terminus, Middle Road narrows down to two lanes, loses its divider, merges with Sound Avenue, and ends. Continue straight ahead to go west on Sound Avenue. If the extension of the Long Island Expressway (I-495) from Riverhead to Mattituck had been built, the western terminus of the expressway would have been here.

Photos taken August 2009.