Delaware 299 overlays U.S. 301 (Middletown Warwick Road) 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 Delaware 299 to an interchange with Delaware 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.

The U.S. 301 Toll road under construction around Middletown will realign Delaware 299 onto a frontage road leading north from Warwick Road. Running north along the west side of the new expressway, Delaware 299 will hook into an extension of Levels Road and a diamond interchange with U.S. 301.

A two year project anticipated to begin in 2019 will improved the capacity of Delaware 299 in Middletown. Expansion will widen the state route into a five-lane boulevard with a continuous center turn lane from Catherine Street to Cleaver Farm Road, and a four-lane divided arterial from Cleaver Farm Road to Delaware 1.

Delaware 4 in southern New Castle County - 1941

The east-west route from the state line near Warwick, Maryland to Middletown and Odessa was designated as Delaware 4 by 1938. Maryland 299 south through Warwick to Massey was established by 1942. Mid-1950s construction of Maryland 71 from U.S. 50 at Queenstown to the Delaware state line by Warwick, coincided with the renumbering of Delaware 4 east to Odessa as Delaware 299 in 1957. The 1959 extension of Delaware 9 north to Wilmington also included lengthening Delaware 299 east from Downtown Odessa to Mathews Corner.

Delaware 4 renumbered as Delaware 299 - 1957

Delaware 71 was realigned to form a multi state route with Maryland 71 as U.S. 301 was extended to Delaware in 1960. Sassafras Road was subsequently decommissioned as Maryland 299 between the new U.S. 301 and Cecilton Warwick Road (Maryland 282). Maryland 299 east through Warwick was renumbered as an extension of Maryland 282, creating a numbering anomally with Delaware 299. Within the First State, U.S. 301 separated into north and south branches between Middletown and Tybouts Corner. U.S. 301 North overlapped with Delaware 299 east to Middletown until 1971.

Delaware 71 was dropped from its overlap with U.S. 301 and Delaware 299 southwest from Middletown after 1984. Delaware 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 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

Delaware 299 east
Delaware 299 (Warwick Road) takes over for Maryland 282 (Main Street) east from the state line along a rural stretch outside the Middletown limits. Photo taken 12/21/01.
U.S. 13 separates into a one-way couplet of 6th and 5th Streets through Odessa. Delaware 299 (Main Street) east intersects U.S. 13 north ahead of the historic district. Photo taken 01/15/17.
Main Street expands to include on-street parking as SR 299 leads away from U.S. 13 (5th Street) north. Photo taken 01/15/17.
Main Street east at 2nd Street. SR 299 makes an S-curve beyond Front Street to leave Downtown. Photo taken 01/15/17.
2 photos
2 photos
Crossing the Appoquinimink River, Delaware 299 lowers across an area of wetlands by the Odessa Access Area. Photos taken 01/15/17.
Old State Road curves southward between the Appoquin Farms subdivisions to Taylors Bridge Road. Delaware 299 turns east while Old State Road loops west to U.S. 13 (Dupont Parkway). Photo taken 01/15/17.
Taylors Bridge Road links Delaware 299 east with Delaware 9 (Thomas Landing Road), 0.18 miles to the east. Photo taken 01/15/17.
Delaware 9 straddles coastal areas of New Castle County southward from Reedy Point Bridge to Flemings Landing and Kent County. The state route also serves several subdivisions built to the east of Odessa and Fieldsboro. Photo taken 01/15/17.
An end shield marks the conclusion of Delaware 299 by the Silver Hill Farms neighborhood. Photo taken 01/15/17.
A historical look at an older shield style for the Delaware 299 eastern terminus. Photo taken 12/21/01.
Delaware 299 west
Warwick Road branches west from U.S. 301 along a rural course 0.52 miles to Main Street through Warwick, Maryland. Construction for the U.S. 301 toll road around Middletown realigns Warwick Road onto a frontage road southwest from Levels Road. Photo taken 08/10/04.
Maryland 282 commences a 12.43 mile route west from Delaware 299 to Cecilton and Crystal Beach. Photo taken 08/10/04.

Photo Credits:

12/21/01, 08/10/04, 01/15/17 by AARoads

Connect with:
U.S. 13
U.S. 301
Delaware 9
Delaware 15
Delaware 71
Maryland 282

Page Updated 02-16-2017.