Maryland Striper Fishing includes two areas: Chesapeake Bay which includes the Potomac River, and the coastal section including beaches around Ocean City and especially the Assateague Island National Seashore. Striped Bass are more likely to be called "Rockfish" in Maryland which is not a bad name as they love structure and are often found near rocks.
Chesapeake Bay probably needs no introduction as it's not only the largest estuary in the United States but the largest spawning area for striped bass, spawning occurring from March to April.
You can catch stripers, better known locally as rockfish, in Chesapeake Bay year round although you must check regulations for fishing seasons, catch and release regulations, etc. A couple of well known places that hold fish year round include the Chesapeake Bay Bridge Tunnel and the Hampton Roads Bridge Tunnel, as well as many lesser known areas. Most of the fishing is along channel edges and public assess is very limited, meaning a boat is needed for most fishing.
Big Chesapeake stripers, the migratory bass, are primarily
available in the winter months, December until March. Most of the fishing is
from boats, and getting out requires the weather to cooperate. Many of the
larger fish, especially on fly rod, are caught at night on the shadow line
around bridges. The shadow line is edge of the bridge shadow cast by the
street lights on the bridges (and typically offer great bass fishing
everywhere, including in my home state of new Hampshire)!
The Assateague Island National Seashore is a major shore fishing area and can be accessed from both Maryland and Virginia. The Maryland access is via Assateague State Park in Maryland, and both walk in and beach buggy access is possible.
Although some stripers are available year round, Assateague Island is primarily a spring and fall fishery, at least for big fish. The fall season runs from mid-September to early or late December, depending on the weather. The spring season starts mid March, Saint Patricks Day (May 17) is mentioned by many locals, until the end of May.
The Ocean City area similar to Assateague Island, except there isn't nearly as much natural structure to bring fish near shore or hold them there.