Maryland Route 445 (MD 445) is a state highway in the U.S. state of Maryland. The state highway runs 11.96 miles (19.25 km) from Eastern Neck Island in the southwest corner of Kent County north to MD 21 in Tolchester Beach. MD 445 connects Tolchester Beach and Eastern Neck Island to Rock Hall, where the highway intersects MD 20. The state highway was constructed around 1930.

MD 445 begins at the north end of the bridge from the mainland to Eastern Neck Island. Eastern Neck Road continues south toward Eastern Neck National Wildlife Refuge. MD 445 heads north through farmland until the highway enters the town of Rock Hall immediately after passing Boundary Street. The state highway is known as Main Street through Rock Hall, where the highway intersects Sharp Street and MD 20 (Rock Hall Avenue). After passing Rock Hall Ball Park, MD 445 leaves the town limits and its name changes to Tolchester Road. The state highway passes through a mix of farms and forests and crosses Swan Creek before reaching its northern terminus at Tolchester Beach Road. Tolchester Beach Road is marked as MD 21 east from the intersection and is a county highway west to the old beach resort, while the roadway continues north as Bay Shore Road.

MD 445 was constructed from Tolchester Beach south through Rock Hall to approximately 1 mile (1.6 km) north of Eastern Neck Island in 1929 and 1930. The remainder of the highway to the north end of the bridge to the island was completed shortly after 1930.

The entire route is in Kent County.