Re: New to boating, live in PA
There are several places on the upper bay to launch.
Charleston Marina (in Charleston, MD) has a public ramp (I don't believe there is a charge) You can access the marina by taking Route 40 to Route 7 which runs right into Charleston.
On Route 272 South you will find Elk neck state park. The park has multiple ramps but there are fees to use. Refer to these sites:
http://www.dnr.state.md.us/publiclands/central/elkneck.html
http://www.dnr.state.md.us/publiclands/oc.html
You are actually puting in at Rogues Harbor. There are 4 lanes at the boat launch so it keeps things moving.
The are many more marinas available that you can use too, most will charge a fee of some kind. A few in North East MD, Some in Georgetown, MD on the Sasafrass River and I believe some in Havre De Grace as well. (Altough if you go to Havre De Grace there will be a fee to use the bridge which will allow you to use it for the next year.)
As far as where to go on the water.... That is an endless possibility!
Check out Havre De Grace, neat town with free transient docks. You can check out 3 lighthouses (Turkey Point, Fishing Battery and Havre De Grace). Boat up the Susquehanna River to Perryville and Port Deposit. Check out the North East river and Chesapeake City in the C & D canal. Tube and ski or just cruise the Bohemia and Sasafrass rivers. As you can see, there are tons of places to go on the Bay and this is just the upper 15(?) miles of the bay!
More on here will be able to tell you more than i can as well. For a good thread on boating the upper chesapeake check out this link under the "boating destinations" area:
http://forums.iboats.com/showthread.php?t=189770
Hope all of this info helps! Have fun out there!