| State: | MD |
| Type: | MD |
| Route: | 353 |
| Map Alt: | A map of the northern part of the lower Eastern Shore of Maryland showing major roads. Maryland Route 353 runs from Pittsville north to the Delaware state line. |
| Map Custom: | yes |
| Map Notes: | Maryland Route 353 highlighted in red |
| Length Mi: | 5.08 |
| Length Round: | 2 |
| Established: | 1927 |
| Direction A: | South |
| Terminus A: | in Pittsville |
| Junction: | in Pittsville |
| Direction B: | North |
| Terminus B: | near Pittsville |
| Counties: | Wicomico |
| Previous Type: | MD |
| Previous Route: | 352 |
| Next Type: | MD |
| Next Route: | 354 |
Maryland Route 353 (MD 353) is a state highway in the U.S. state of Maryland. Known for most of its length as Gumboro Road, the state highway runs 5.08miles from U.S. Route 50 (US 50) just south of Pittsville north to the Delaware state line, where the highway intersects Delaware Route 26 (DE 26) and DE-MD 54. MD 353 was constructed in the mid- to late 1920s. The route was extended south from MD 346 to US 50 in Pittsville in 2016.
MD 353 begins at an intersection with US 50 (Ocean Gateway) just south of Pittsville, heading northeast on two-lane undivided Sixty Foot Road, which continues south as a county highway past US 50. Upon crossing MD 346 (Old Ocean City Road), the road name changes to Gumboro Road and MD 353 heads through the town of Pittsville. After intersecting Main Street, the highway turns north past scattered residences. After crossing Aydelotte Branch, MD 353 leaves Pittsville, crossing Burnt Mill Branch and passing through farmland all the way to the highway's northern terminus at the Delaware state line. The roadway continues into Delaware as DE 26 and DE 54 (Millsboro Highway). East Line Road heads east from the intersection at the state line, while DE-MD 54 (East Line Road) follows the state line west to the towns of Delmar, Maryland, and Delmar, Delaware.
MD 353 was constructed as a modern highway beginning in 1925 from Pittsville. By 1927, the highway extended north to Burnt Mill Branch. MD 353 was completed to the Delaware state line in 1929. On April 20, 2016, the portion of Sixty Foot Road between US 50 and MD 346 was transferred from county and town maintenance to state maintenance and became a southern extension of MD 353.