Maryland Route 299
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Maryland Route 299 highlighted in red
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| Route information | ||||
| Maintained by MDSHA | ||||
| Length: | 5.67 mi (9.12 km) | |||
| Existed: | 1929 – present | |||
| Major junctions | ||||
| South end: |
  MD 313 / MD 330 at Massey
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 MD 290 at Sassafras
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| North end: |
 US 301 near Warwick
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| Location | ||||
| Counties: | Kent, Cecil | |||
| Highway system | ||||
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Maryland Route 299 (MD 299) is a state highway in the U.S. state of Maryland. The highway runs 5.67 miles (9.12 km) from MD 313 and MD 330 at Massey in eastern Kent County north to U.S. Route 301 (US 301) near Warwick in far southern Cecil County. MD 299 was constructed from Massey to Sassafras around 1930 and from there to MD 282 in Warwick in the early 1930s. The highway between US 301 and MD 282 was transferred to county control in 1958.
MD 299 begins at a four-way intersection with MD 313 and MD 330 at the hamlet of Massey in eastern Kent County. MD 313 heads west as Galena Massey Road and south as Millington Massey Road, and MD 330 heads east as Massey Delaware Line Road. MD 299 heads north as two-lane Massey Road and immediately has a grade crossing of the Chestertown Branch of the Northern Line of the Maryland and Delaware Railroad just west of the junction of the Centreville and Chestertown branches of the Northern Line. The highway crosses Jacobs Creek before an intersection with the northern terminus of MD 290 (Galena Sassafras Road). MD 299 continues northeast as Galena Sassafras Road, which passes the historic home Rich Hill and crosses Herring Branch into the village of Sassafras. At the north end of the village, the highway crosses the Sassafras River into Cecil County, where the name of the highway changes to Massey Sassafras Road. MD 299 reaches its northern terminus at US 301 (Blue Star Memorial Highway). Sassafras Road continues northeast toward the village of Warwick.
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