Delaware 299 Guide - Highway Guides for Delaware Interstates - U.S. Routes - State Routes

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The Guide to Delaware State Route 299

The path of Delaware 299 existed as the first version of Delaware 4 between 1938 and 1959. In 1959 Delaware 4 became Delaware 299 to coincide with Maryland 299 along Warwick Road. From there the route traveled between the Maryland state line, Middletown, and Odessa via the current alignment of Delaware 299. This entails Middletown Warwick Road (U.S. 301), Main Street, Middletown Odessa Road, Old State Road and Taylors Bridge Road.

Delaware 299 shares 2.5 miles of pavement with U.S. 301 between Warwick Road and Middletown (pop. 6,161). Delaware 15 joins the tandem between Levels Road and Bunker Hill Road for 1.1 miles. In 1993 a new alignment bypassed Middletown to the west for U.S. 301. At that time the 0.6-mile cosigning of U.S. 301 & Delaware 299 along Main Street to Delaware 71 (Broad Street) ceased to exist. In 1999 an interchange opened along the SR 1 Turnpike with Delaware 299 at Odessa.

The extension of U.S. 301 from Bowie, Maryland to Farnhurst, Delaware in the late 1959s vastly replaced Maryland 299 as the main route between Millington, Massey, Warwick, and Middletown. Sometime after U.S. 301 overtook Maryland 71, Maryland 299 was truncated from the Delaware state line three miles to the southwest at the intersection of Sassafras Road with U.S. 301. Maryland 282 then overtook Warwick Road from Sassafras Road at Warwick eastward to Delaware 299. So the effort to have a common number between the two states was short lived.

Delaware 299 Mileage Table

Western Terminus Eastern Terminus Names Mileage
Maryland state line (Maryland 282) Delaware 9 - Mathews Corners Warwick Road, Middletown Warwick Road, Main Street, Middletown-Odessa Rd, Old State Road, Taylors Bridge Road 9.79

Delaware 299 2002 Annual Average Daily Traffic (AADT)

  • 1,868 - Maryland state line to U.S. 301
  • 14,399 - U.S. 301 overlap
  • 10,098 - Peterson Road to Delaware 71/North Broad Street (Middletown)
  • 5,882 - east Middletown limits to west Odessa limits
  • 784 - east Odessa limits to Road 449

Delaware 299 Terminus Collection

Western terminus
The first Delaware 299 shield posted on Warwick Road at the Maryland state line. Warwick Road travels east from Warwick, Maryland as Maryland 282 to the state border. From here Delaware 299 travels one half mile to the merge with U.S. 301 (Middletown Warwick Road). Photo taken 12/21/01.
Eastern Terminus
Delaware 299 draws to a close 1.7 miles southeast of junction U.S. 13 (Dupont Highway) and Odessa (pop. 286). Old State Road carries the state highway from Odessa by new subdivisions to Taylors Bridge Road. A quick turn onto Taylors Bridge Road brings Delaware 299 to its east end at junction Delaware 9 (Thomas Landing Road). Photo taken 12/21/01.

Delaware 299 Highway Guide

Delaware 299 Southbound
Delaware 299 turns onto Warwick Road for a 0.6-mile drive from U.S. 301 to the Maryland state line. The two-lane rural roadway features full shoulderson the treck to Warwick, Maryland and Maryland 282. Photo taken 08/10/04.
Delaware 299 (Warwick Road) transitions into Maryland 282 at the state line. Maryland 282 from there travels to Warwick, Cecilton, Earlville, and Crystal Beach. Old Maryland 299 splits from Maryland 282 0.9 miles ahead via Sassafras Road to junction U.S. 301 and Maryland 299's northern terminus. Photo taken 08/10/04.

Delaware 299 Other Highway Sites

Page Updated September 4, 2004
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