OCMD is awesome! Lots of restaurants and bars right on the bay with docks.
Fager's Island is very nice and food is somewhat reasonable. They play the 1812 Overture during the brillant sunsets over the bay, and everyone applauds at the end! Perfectly timed to end just as the sun dips below the horizon.
Fishtales is a great open air bar and grill, tables out on the sand and a pirate ship for the kids to climb on.
Seacrets is more of a younger crowd club-like atmosphere. I think they have a radio station on site that runs like a dance club in the evenings. You can hear the music from the channel as you motor by, so you can't miss it. Chicks are hot there, BTW.
In West Ocean City, if you like seafood, you definitely need to check out
Watermans. They have an all you can eat thing going where they continue to "dump" king crab legs, blue crabs, chicken, corn on the cob, hush puppies, etc. You defintely walk away from there very happy.
There's also a Phillips Seafood Restuarant (the same as from the Baltimore) there, which has the best Lobster Bisque I've ever had.
We found that there are so many places to eat in OC that we never had to wait long to get a table.
Assateague Island is very nice. There's wild ponies on the island, and they are very tame. You can actually pet them (although the rangers discourge this). Every year, the third week in July, the Ocean City, MD fire department swims the ponies across the bay for an auction. It gets pretty wild around that time, lots of boaters out there to see the show.
The boardwalk gets VERY crowded. If you have kids, go in the afternoon and get out of there before 7PM. It's a zoo. Lots of rides, Hard Rock Cafe, Ripley's Believe It Or Not Museum (make sure to try to make the funnny faces in the mirror in the beginning!) are all on the boardwalk.
And of course, I have vast experience and knowledge of the inlet. It was very easy to negotiate, not too busy, and very well marked. Once in the bay, stay in the channel as it gets very shallow real fast.
Annabo has found the bottom more than once in that bay!