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, three years of construction improved capacity along SR 299 in Middletown. Utility relocation for the expansion project got underway in Spring 2020. Work through Fall 2023 Spring 2024 widened 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. Construction was substantially complete
The alignment of SR 299 from the state line near Warwick, Maryland to Middletown and Odessa was designated as SR 4 by 1938. MD 299 south through Warwick to Massey was established by 1942. Construction of MD 71 in the mid 1950s, from U.S. 50 at Queenstown to the Delaware state line by Warwick, coincided with the renumbering of SR 4 east to Odessa as SR 299 in 1957. The 1959 extension of SR 9 north to Wilmington also included lengthening SR 299 east from Downtown Odessa to Mathews Corner.
SR 4 renumbered as SR 299 - 1957
SR 4 in southern New Castle County - 1941
SR 71 was realigned to form a multi state route with MD 71 as U.S. 301 was extended to Delaware in 1960. Sassafras Road was subsequently decommissioned as MD 299 between the new U.S. 301 and Cecilton Warwick Road (MD 282). MD 299 east through Warwick was renumbered as an extension of MD 282, creating a numbering anomally with SR 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 SR 299 east to Middletown until 1971.
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
 East |
 | SR 299 (Warwick Road) takes over for MD 282 (Main Street) east from the state line along a rural stretch outside the Middletown limits. 12/29/17 |
 | The realignment of SR 299 made in 2017 shifted the state route northward from its previous intersection with U.S. 301, located by this reassurance marker, toward Middle Neck Road. 12/29/17 |
 | SR 299 (Warwick Road) parallels the southbound lanes of U.S. 301 (First Responders Memorial Highway) to Middle Neck Road. Middle Neck Road (Rd 444) angles northwest to agricultural areas outside the Middletown city limits. 12/29/17 |
 | The third shield for SR 299 east stands beyond the intersection with Middle Neck Road. 12/29/17 |
 | SR 299 (Warwick Road) navigates through a broad curve into the diamond interchange (Exit 2) with U.S. 301 (First Responders Memorial Highway). 12/28/20 |
 | The toll road along U.S. 301 extends 9.3 miles northeast to SR 1 ahead of St. Georges. Annapolis, Maryland lies 65 miles to the southwest. 12/28/20 |
 | U.S. 301 (First Responders Memorial Highway) uses all electronic toll (AET) collection with E-Zpass transponders or pay-by-plate. 12/28/20 |
 | Located 27 miles to the northeast, U.S. 301 to SR 1 connects with Interstate 95 north to Wilmington. 12/28/20 |
 | Continuing from the east side ramps with U.S. 301, SR 299 (Warwick Road) advances to Middletown Warwick Road and SR 15 (Levels Road). 12/28/20 |
 | SR 15 follows Levels Road south to Charles E. Price Memorial Park and Dogtown Road to the west of Townsend. 12/28/20 |
 | SR 15 north combines with SR 299 east along Middletown Warwick Road (old U.S. 301) toward central Middletown. 12/28/20 |
 | SR 15 comprises a rural route connecting Middletown with Clayton in Kent County. Northward, SR 15/299 (Middletown Warwick Road) overlap for 1.05 miles to W Main Street. 12/28/20 |
 North East |
 | SR 15/299 east advance northeast along a commercialized stretch lined with restaurants, big box retail and gas stations. The first shields for the overlap stand east of Levels Road. 12/16/17 |
 | Merrimac Avenue constitutes a four lane boulevard south to an area of warehouses and distribution centers and north through the Westown retail area to the Parkway development. 12/16/17 |
 | SR 15/299 (Middletown Warwick Road) east continue by Westown center into central Middletown. 12/16/17 |
 | South Ridge Avenue connects SR 15/299 (Middletown Warwick Road) with additional retail and the Parkway community. 12/16/17 |
 | SR 15 turns west along Bunker Hill Road from SR 299 and Middletown Warwick Road (old U.S. 301) at W Main Street. Bunker Hill Road spans the U.S. 301 toll road west to Choptank Road. 12/16/17 |
 | SR 299 follows Main Street east from SR 15 and Middletown Warwick Road through Downtown Middletown. 12/16/17 |
| East |
 | W Main Street narrows from four to two lanes just east of Middletown Warwick Road (old U.S. 301) and this confirming marker for SR 299. 12/28/20 |
 | The town of Odessa lies 3.5 miles east along SR 299 from SR 15 and Middletown Warwick Road (former U.S. 301). 12/28/20 |
 | Industrial Drive loops south and west to industrial businesses and distribution centers between this traffic light on SR 299 (W Main Street) and SR 15 (Levels Road). 12/28/20 |
 | W Main Street east at Downtown Middletown. 12/28/20 |
 | SR 71 crosses SR 299 (Main Street) along Broad Street. Unmarked along both directions of Main Street, SR 71 heads north to Mount Pleasant and south to Townsend. 12/28/20 |
 | Catherine Street intersects SR 299 (E Main Street) four blocks north of Silver Lake Park. 12/28/20 |
 | 2021-23 construction expands SR 299 (E Main Street) from two to five lanes east from Catherine Street in Middletown. 12/28/20 |
 | The Odessa town center lies 2.5 miles east of New Street along SR 299. 12/28/20 |
 | Clever Farm Road south and Dickenson Boulevard north come together at the succeeding traffic light along SR 299 (E Main Street) eastbound. 12/28/20 |
 | Silver Lake Road (Rd 442) stems 1.11 miles south from SR 299 (E Main Street) to Noxontown Road (Rd 38) across Silver Lake. 12/28/20 |
 | Road work through 2023 widens SR 299 to a four lane, divided arterial east from Silver Lake Road to the exchange with SR 1. 12/28/20 |
 | Dove Run Boulevard heads south from the Dove Run Estates division to intersect SR 299 (Main Street) across from Middletown High School. 12/28/20 |
 | Brick Mill Road (Rd 430) heads 1.14 miles north from SR 299 at Willow Grove Mill Drive to Marl Pit Road (Rd 429). Willow Grove Mill Drive represents the main entrance to the Longmeadow development. 12/28/20 |
 | Reassurance marker posted east of Brick Mill Road. 12/28/20 |
 | Gloucester Boulevard leads south to the Willow Grove Mill development from SR 299 opposite the access road to the ChristianaCare Middletown Free-standing Emergency Department. 12/28/20 |
 | SR 299 (Middletown Odessa Road) expands to four lanes through the diamond interchange (Exit 136) with SR 1 (Korean War Veterans Memorial Highway). 12/28/20 |
 | The toll road along SR 1 travels south from Odessa to Smyrna and Dover. 12/28/20 |
 | SR 1 wraps around the west side of Odessa northward to St. Georges, Bear and I-95 at Churchmans Crossing. 12/28/20 |
 | Tolls are collected along SR 1 north at the exchange with Pole Bridge Road at Boyds Corner and on the mainline at the Biddles Corner Toll Plaza. 12/28/20 |
 | SR 299 (Middletown Odessa Road) enters the town of Odessa a quarter mile from the ramps with SR 1 (Korean War Veterans Memorial Highway). 12/28/20 |
 | SR 299 curves east along Main Street to Odessa Memorial Park and U.S. 13. U.S. 13 separates into the one way couplet of 6th and 5th Streets through Odessa. 12/28/20 |
 | U.S. 13 (6th Street) travels south from Odessa to the town of Smyrna. The town of Townsend is located to the southwest from U.S. 13 via Pine Tree Road. 12/28/20 |
 | SR 299 (Main Street) east intersects U.S. 13 (5th Street) north to Boyds Corner ahead of the Odessa historic district. 01/15/17 |
 | Main Street expands to include on-street parking as SR 299 leads away from U.S. 13 (5th Street) north. 01/15/17 |
 | Main Street east at 2nd Street. SR 299 makes an S-curve beyond Front Street to leave Downtown. 01/15/17 |
  | Crossing the Appoquinimink River, SR 299 lowers across an area of wetlands by the Odessa Access Area. 01/15/17 |
 | Old State Road curves southward between the Appoquin Farms subdivisions to Taylors Bridge Road. SR 299 turns east while Old State Road loops west to U.S. 13 (Dupont Parkway). 01/15/17 |
 | Taylors Bridge Road links SR 299 east with SR 9 (Thomas Landing Road), 0.18 miles to the east. 01/15/17 |
 | SR 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. 01/15/17 |
 | An end shield marks the conclusion of SR 299 by the Silver Hill Farms neighborhood. 01/15/17 |
 | An older shield style end shield for SR 299 previously posted at SR 9. 12/21/01 |
| West |
 | Leaving the town of Odessa, SR 299 (Middletown Odessa Road) continues 2.7 miles to Downtown Middletown and seven miles to the Maryland state line ahead of Warwick. 12/28/20 |
 | Advancing west, SR 299 (Middletown Odessa Road) enters a diamond interchange with SR 1 (Korean War Veterans Memorial Highway). 12/28/20 |
 | SR 1 (Korean War Veterans Memorial Highway) is a toll road extending seven miles north to South St. Georges and 26 miles south to Dover Air Force Base. 12/28/20 |
 | SR 1 travels south from Middletown and Odessa to Smyrna, Dover and Milford. 12/28/20 |
 | SR 1 (Korean War Veterans Memorial Highway) opened to traffic south from SR 299 to Smyrna in May 2003 and north to St. Georges in November 1999. 12/28/20 |
 | SR 299 enters the town limits of Middletown west of SR 1 at Gloucester Boulevard south. 12/28/20 |
 | Brick Mill Road (Rd 430) extends 1.14 miles north from Willow Grove Mill Drive at SR 299 to Marl Pit Road (Rd 429). 12/28/20 |
 | SR 299 (Middletown Odessa Road) advances west between Dove Run Shopping Center and the athletic fields for Middletown High School. 12/28/20 |
 | Silver Lake Road (Rd 442) runs 1.11 miles south from SR 299 (E Main Street) by Middletown Crossing shopping center to Silver Lake and Noxontown Road (Rd 38). 12/28/20 |
 | 2021-23 expansion of SR 299 widens E Main Street to a four lane, divided arterial west to forthcoming Clever Farm Road. 12/28/20 |
 | Clever Farm Road spurs north from SR 299 at Dickenson Boulevard to the Villagebrook mobile home community. 12/28/20 |
 | Widening of SR 299 (E Main Street) extends west to Catherine Street. Catherine Street runs along the east side of the Middletown street grid to Silver Lake Park. 12/28/20 |
 | SR 299 (Main Street) intersects SR 71 (Broad Street) in Downtown Middletown. SR 71 follows Broad Street 0.98 miles north onto Summit Bridge Road (old U.S. 301). South from Middletown, SR 71 runs 5.73 miles to Townsend and U.S. 13 at H & H Corner. 12/28/20 |
 | SR 299 (W Main Street) crosses a Norfolk Southern Railroad line west ahead of the traffic light with Industrial Drive and the entrance to Market Place shopping center. 12/28/20 |
 | SR 299 (W Main Street) expands to a four lanes leading into the intersection with SR 15 at Bunker Hill and Middletown Warwick Roads. Prior to January 2019, Middletown Warwick Road was a part of U.S. 301 south into Maryland and north to Summit Bridge Road. 12/28/20 |
 | SR 15 branches 1.01 miles west from Middletown Warwick Road 1.01 along Bunker Hill Road to a roundabout with Choptank Road and School Drive to Appoquinimink High School. 12/28/20 |
| South West |
 | SR 299 west and SR 15 south overlap for 1.05 miles from W Main Street to Warwick Road along Middletown Warwick Road (old U.S. 301). 12/28/20 |
 | South Ridge Avenue connects SR 15/299 (Middletown Warwick Road) with adjacent retail and the Parkway development. Diamond State Boulevard ties in from additional big box stores to the east. 12/28/20 |
 | Reassurance markers for SR 15 south / SR 299 west posted by Westown retail plaza. 12/28/20 |
 | The succeeding traffic light along Middletown Warwick Road southbound is with Merrimac Avenue north to the Parkway development and south to Industrial Drive. 12/28/20 |
 | A final set of shields for the SR 15/299 overlap stand west of Merrimac Avenue by additional areas of Westown center. 12/28/20 |
  | Advancing west, SR 299 meets U.S. 301 (First Responders Memorial Highway) just after the northward turn at Levels Road. 12/28/20 |
  | SR 15 south and SR 299 west part ways with old U.S. 301 (Middletown Warwick Road) for Levels Road and Warwick Road respectively. 12/28/20 |
 | U.S. 301 bypasses Middletown along the tolled First Responders Memorial Highway south to the Maryland state line and northeast to SR 1 at Biddles Corner. 12/28/20 |
| West |
 | SR 299 branches northwest from SR 15 (Levels Road) and Middletown Warwick Road (old U.S. 301) to cross over U.S. 301. 12/28/20 |
  | A diamond interchange (Exit 2) joins SR 299 with U.S. 301 (First Responders Memorial Highway). 12/28/20 |
 | Opened in January 2019, the toll road bypasses Middletown to the west en route to SR 1 north ahead of St. Georges. 12/28/20 |
 | U.S. 301 continues 11.5 miles south from Middletown uninterrupted to MD 299 (Sassafras Road) near Sassafras. Through the Eastern Shore of Maryland, U.S. 301 constitutes an expressway southwest to U.S. 50 and the Chesapeake Bay Bridge. 12/28/20 |
 | SR 299 (Warwick Road) curves southwest from the U.S. 301 Wetlands Mitigation Site to run along the west side of the First Responders Memorial Highway toward the Maryland state line. 12/28/20 |
 | Middle Neck Road ties into SR 299 (Warwick Road) from Cecil County, Maryland ahead of this shield assembly. 12/15/17 |
 | Rejoining the original alignment of Warwick Road, SR 299 leads away from U.S. 301 one mile to unincorporated Warwick. The town of Cecil follows in five miles at MD 213. 12/15/17 |
 | The last reassurance marker for SR 299 westbound. 12/15/17 |
 | MD 282 commences a 12.43 mile route west from SR 299 to Cecilton and Crystal Beach. This shield assembly was removed by 2017. 08/10/04 |
Connect with:
U.S. 13
U.S. 301
State Route 1
State Route 9
State Route 15
State Route 71
Route 282
Page Updated 03-01-2021.