I would probably go that way (295/penn)- that's how I typically get to 50 to head to the beach. (I live in Arlington, work in DC.) If leaving from DC, I typically take MD Ave through Capitol Hill to 50, but I think the other way would be faster from VA.

also, if you can leave by 2:00 and then kill time (coffee, drink, whatever) once you get into Annapolis, you'll probably be happier. that said, it's not summer so you might not have to worry about it.

I'd grab the GW parkway to the beltway and drive around to rt 50. But I'd do nearly anything to avoid driving through the city to Annapolis (we live near McLean beltway entrance). Also, I'd leave as early as you can and hope to have extra time for a drink before the service.

I have to go to Annapolis for a memorial next week that starts at 5:00pm. I know that any way I pick will suck, I'm just trying to figure out the lowest level of suck. I have to pick up a cousin at the Key Bridge Marriot. 295 to the little jog on Penn Ave to 50? Is there any other way? I know going through town on NY Ave would be worse, right? Thanks.