Not a problem at all. I’ve done Annapolis out across the bridge, up the trail, and then back. I highly recommend bombing down the hill right before the bridge and hoping for a green light.
There’s a nice wide shoulder most of the way, and if you turn left at the first light past the bridge, it’ll take you straight downtown.
I didn’t think I could find the Strava route I took but then I did.
I will warn you that pedestrians on the trail are more like Gravely Point gawkers than those out for exercise on the W&OD – give them extra time to react and expect cluelessness.