Delaware Route 299

Delaware Route 299
Route information
Maintained by DelDOT
Length	9.77 mi[1] (15.72 km)
Existed	1957[2][3]–present
Tourist routes	Harriet Tubman Underground Railroad Byway Delaware Bayshore Byway
Major junctions
West end	MD 282 near Warwick, Maryland
Major intersections	US 301 Toll in Middletown DE 15 in Middletown DE 71 in Middletown DE 1 Toll in Middletown US 13 in Odessa
East end	DE 9 in Mathews Corners
Location
Country	United States
State	Delaware
Counties	New Castle
Highway system
Delaware State Route System List Byways
← I-295 → DE 300

Delaware Route 299 (DE 299) is a 9.77-mile-long (15.72 km) state highway in New Castle County, Delaware. It runs from Maryland Route 282 (MD 282) at the Maryland state line east of Warwick, Maryland to DE 9 in Mathews Corners, traveling through Middletown and Odessa. The route intersects the U.S. Route 301 (US 301) toll road, DE 15, and DE 71 in Middletown, the DE 1 toll road east of Middletown, and US 13 in Odessa. The highway travels through a mix of suburban development and some farmland.

DE 299 was originally designated as DE 4 in 1938, traveling as far east as US 13 in Odessa. By 1957, DE 4 became DE 299 to match MD 299 (now MD 282) and was extended east to DE 9 in 1959. Over the years, several different highways had followed the DE 299 alignment including DE 71 west of Middletown between 1959 and 1987, US 301N between Middletown and Odessa from 1959 to 1971, and US 301 west of Middletown between 1959 and 2019. In 2008, a widening of DE 299 in the western part of Middletown began; it was completed in November 2010. A portion of the route west of Middletown was realigned in 2017 as a result of the construction of the US 301 toll road.