Early September you have the some of the last cobia leaving the bay. Late to the end of September big red drum start moving south. Past 2 years the last weekend in September has put drum on little island pier. This year it may be the first weekend of October. Other than that, spot, Whiting , black drum, shark. most stuff should be munching around then.
You have a better chance at the foot of the cbbt for bass. Not saying that they don't show but I've personally never caught a bass to brag about from shore on this side of the lower bay/ocean. You're going to be more productive fishing bait for drum or cobia if you're looking for large fish.
Yes and no.... they exist.. but are hard to get to. Some of the lower island's are reachable by water taxi or kayak. The easiest to access is assateague/ chincoteague... you can drive on. For bass you could likely have a shot for them end of September ish depending on water temperature and bait fish
Assateague is split between Maryland and Virginia. Each state has different regulations for osv. your permit is good for both states, you can't drive the beach from one state to the other. Maryland has over night, Virginia only to 10pm. Va has a north and a south osv sections. The north osv is open year round the south osv gets closed to different degrees for birds and turtles. The walk on portion in Virginia can get over the top with tourist in the summer making it impossible to fish. Imagine a couple thousand people in a mile-ish section of beach with no regard to anyone else's personal space or existence. But it does get better in the fall. However the parking lot also shrinks considerably at this time making long walks to get to some areas
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