State Route 299 West

SR 299 turns north onto Old State Road (Rd 441) from Taylors Bridge Road 0.18 miles west of SR 9 (Thomas Landing Road).

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SR 299 lines a causeway across wetland areas west from Old Corbit Road (Rd 424) to the Appoquinimink River.

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Entering the town of Odessa, SR 299 lines Main Street west through the historic district.

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U.S. 13 (DuPont Parkway) partitions into a couplet through Odessa. SR 299 (Main Street) crosses the US highway west of 4th Street.

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SR 299 (Main Street) connects U.S. 13 (DuPont Parkway) and Odessa with SR 1 (Korean War Veterans Memorial Highway) 0.71 miles to the west.

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Generally serving local traffic, U.S. 13 (DuPont Parkway) north from Odessa leads to Boyds Corner and Saint Georges.

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SR 299 confirming marker posted west between the signalized intersections with U.S. 13.

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South from Odessa, U.S. 13 travels to the Delaware capital city of Dover and Salisbury, Maryland.

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Paralleling SR 1, U.S. 13 passes Townsend south to Smyrna and Cheswold in Kent County.

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Heading out of Odessa, SR 299 (Main Street) curves southwest to SR 1.

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West from Odessa, SR 299 (Middletown Odessa Road) continues 2.7 miles to Downtown Middletown and seven miles to the Maryland state line ahead of Warwick.

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Advancing west from Marcus Road, SR 299 (Middletown Odessa Road) enters a diamond interchange (Exit 136) with SR 1 (Korean War Veterans Memorial Highway).

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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.

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SR 1 travels south from Middletown and Odessa to Smyrna, Dover and Milford.

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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.

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SR 299 enters the town limits of Middletown west of SR 1 at Gloucester Boulevard south.

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Gloucester Boulevard spurs south to the Willow Grove Mill development.

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Brick Mill Road (Rd 430) extends 1.14 miles north from Willow Grove Mill Drive at SR 299 to Marl Pit Road (Rd 429).

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SR 299 (Middletown Odessa Road) advances west between Dove Run Shopping Center and the athletic fields for Middletown High School.

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Dove Run Boulevard loops 0.55 miles northeast through the Estates at Dove Run development to Brick Mill Road (Rd 430).

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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).

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2021-23 expansion of SR 299 widens E Main Street to a four lane, divided arterial west to forthcoming Clever Farm Road.

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Clever Farms Road spurs north from SR 299 at Dickenson Boulevard to the Villagebrook mobile home community.

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Road work widening SR 299 along Main Street in Middletown included the addition of traffic lights at New Street.

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The 2021-23 expansion of SR 299 (E Main Street) extended west to Catherine Street. Catherine Street runs along the east side of the Middletown street grid to Silver Lake Park.

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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.

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Main Street west ahead of Cass Street in Downtown Middletown.

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An at-grade crossing with the Delmarva Central Railroad along SR 299 lies west between Wood Street and Peterson Road.

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SR 299 (W Main Street) west next intersects Industrial Drive at the entrance to Market Place shopping center.

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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.

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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.

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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).

12/25/25

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.

12/25/25

Reassurance markers for SR 15 south / SR 299 west posted by Westown retail plaza.

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The succeeding traffic light along Middletown Warwick Road southbound is with Merrimac Avenue north to the Parkway development and south to Industrial Drive.

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A final set of shields for the SR 15/299 overlap stand west of Merrimac Avenue by additional areas of Westown center.

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Advancing west, SR 299 meets U.S. 301 (First Responders Memorial Highway) just after the northward turn at Levels Road.

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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.

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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.

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SR 299 branches northwest from SR 15 (Levels Road) and Middletown Warwick Road (old U.S. 301) to cross over U.S. 301.

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A diamond interchange (Exit 2) joins SR 299 with U.S. 301 (First Responders Memorial Highway).

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Opened in January 2019, the toll road bypasses Middletown to the west en route to SR 1 north ahead of St. Georges.

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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.

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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.

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Middle Neck Road ties into SR 299 (Warwick Road) from Cecil County, Maryland ahead of this shield assembly.

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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.

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The last reassurance marker for SR 299 westbound.

12/25/25

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