Maryland 299 links the town of Massey with the village of Sassafras between the Maryland 313 and U.S. 301 corridors. The state route joins Maryland 213 as the only highways to cross into Kent County from Cecil County to the north. Maryland 299 once continued northward of U.S. 301 via Sassafras Road to Cecilton Warwick Road and through Warwick to the Delaware state line. The highway saw truncation to U.S. 301 and Maryland 282 overtook the Cecilton Warwick Road alignment from the New Castle County line westward. Although disjointed from its cousin in Maryland, a companion Delaware 299 remains signed in Delaware.
Junction Maryland 299 shield posted on Maryland 313 (Galena Road) as it enters the town of Massey. The intersection ahead sees both Maryland 299 and 330 begin. Maryland 299 continues Galena Road northward to Sassafras. Maryland 330 follows Maryland Line Road eastward to Delaneys Corner, Delaware. Photo taken 04/13/04.
Maryland 313 and Galena Road turn westward to junction U.S. 301 and the town of Galena. Maryland 299 begins via Massey Road straight ahead parallel to U.S. 301. Maryland 330 becomes Clayton Delany Road on the 10-mile drive to Clayton and Smyrna in northern Kent County, Delaware. The community of Massey lies at the split of the MDDE Railroad. Photo taken 04/13/04.
Maryland 299 (Massey Road) northbound as it departs Massey and junction Maryland 313 & 330. The MDDE Railroad crosses Massey Road as the state highway leaves town. 4.1 miles to the north is the eastern terminus of Maryland 290 (Galena Sassafras Road). Photo taken 04/13/04.
Northern Terminus - U.S. 301 north of Sassafras
Maryland 299 (Sassafras Road) draws to a close at junction U.S. 301 (Blue Star Memorial Highway) north of Sassafras itself. The state route ends but Sassafras Road continues northward 2.3 miles through Ginns Corner to merge with Maryland 282 (Cecilton Warwick Road). Photo taken 04/13/04.
Looking back from the confluence of U.S. 301, Sassafras Road, and Edgar Price Road at the first southbound Maryland 299 reassurance shield. Sassafras lies 0.9 miles ahead at the intersection with Sassafras Caldwell Road on the Sassafras River. Photo taken 04/13/04.
U.S. 301 southbound at the 0.25-mile sign for junction Maryland 299 (Sassafras Road) in southern Cecil County. Maryland 299 originally continued north of U.S. 301 to the village of Warwick and into Delaware as Delaware 299. The highway was truncated to U.S. 301 and Maryland 282 now encompasses the former routing between the state line and Warwick. Sassafras Road between Warwick and Delaware 299 is not assigned a route number. Photo taken 09/25/04.
Maryland 299 southbound shield posted within the median of U.S. 301 (Blue Star Memorial Highway) for southbound. Maryland 299 travels Sassafras Road 0.75 miles to the hamlet of Sassafras in northern Kent County. Although not in view, a short frontage road (Edgar Price Road) stems northward from Maryland 299 to Levels Road in Delaware. Photo taken 09/25/04.
Maryland 299 2003 Average Annual Daily Traffic (AADT)
1,325 - Maryland 313 & 330 (Massey) to Maryland 290
1,025 - Maryland 290 to U.S. 301
Source: 2003 Highway Location Reference file for Cecil County (MDSHA)
Maryland 299 Guide
Maryland 299 North
Maryland 299 northbound on Sassafras Road after its intersection with Quinn Road north of Massey. The two-lane roadway traverses farm fields and stands of trees between Massey and Sassafras. Photo taken 04/13/04.
Maryland 299 South
Maryland 290 (Galena Sassafras Road) departs Maryland 299 southbound for the town of Galena. The state highway begins here and interchanges with U.S. 301 just west of Sassafras Road. Maryland 290 loops 17.1 miles west of U.S. 301 through Galena, Chesterville, and Crumpton before ending at Maryland 300 outside of Sudlersville. Photo taken 04/13/04.
