SR 299 extends northeast from MD 282 along Warwick Road to U.S. 301 and Middletown Warwick Road (former U.S. 301) from just east of Warwick, Maryland to Main Street in Middletown. Main Street takes the route east through Downtown and suburban areas annexed to the east. Middletown Odessa Road continues SR 299 to an interchange with SR 1 (Korean War Veterans Memorial Highway) and Main Street through Historic Odessa. The route concludes southeast of the Appoquinimink River at semi rural Mathews Corner.
Construction for the the U.S. 301 toll road (First Responders Memorial Highway) around Middletown realigned SR 299 (Warwick Road) onto a frontage road leading north from the Maryland line. Running along the west side of the expressway, SR 299 hooks into a diamond interchange with U.S. 301 and an extension of Levels Road.
Started in July 2021, two years of construction improve capacity along SR 299 in Middletown. Utility relocation for the expansion project got underway in Spring 2020. Work through Fall 2023 widens the state route into a five lane boulevard with a continuous center turn lane from Catherine Street to Cleaver Farm Road, and into a four lane divided arterial from Cleaver Farm Road to SR 1.
SR 71 was dropped from an overlap with U.S. 301 and SR 299 southwest from Middletown after 1984. SR 15 was added along both routes from Levels Road to Bunker Hill Road in 1993. Construction of the new arterial bypass for U.S. 301 west of Peterson Road reconfigured Middletown Warwick Road, Main Street and Bunker Hill Road into a new intersection by the following year.
Delaware State Route 299 - 2015 Annual Average Daily Traffic (AADT)
- 3,265 - Maryland line to U.S. 301
- 15,745 - SR 15 to Peterson Road
- 20,663 - U.S. 301 to east Middletown limits
- 24,282 - east Middletown limits to west Odessa limits
- 13,190 - west Odessa limits to U.S. 13
- 4,137 - U.S. 13 to east Odessa limits
- 746 - Old State Road to SR 9
Page Updated 03-01-2021.