I live on Kent Island. Great place. There are a lot of waterside places including The Jetty (Ghecko Inn), Crab Deck, The Shanty, Red Eyes, and Bay Bridge Beach Club. Thursday nights the Crab Deck has "Thirsty Thursday" which gets a huge crowd and has great happy hour stuff going on. It might have ended at Labor Day though. The Jetty is my favorite place and they have happy hour every night from 4-7. At night it is probably the best of the bunch too. Red Eyes is OK but you might as well go to Ocean City. The only time there are really performance boats there is Sunday, and all you will find there are the sunburned tourists. The Shanty is at the end of the dock at a diner type of place called Anglers. It is literally a shack at the end of a dock but worth having a few beers at.
We will probably crank up the 22' Donzi Blackhawk and head over to the Crab Deck on Thursday then to the Jetty.