Hey, fellow Old Bay enthusiast! Sadly, the brick and mortar stores are few and far between. Most of the tobacco shops around the Baltimore area are, well, "tobacco" shops. You might check out Davidus, there's a few around. Mostly a few C&D, Pease, and Peterson tins with a couple jars of C&D, Lane, and a Stokkebye along the back. The one in Westminister is very good for pipes, the manager there smokes one. But mostly they are cigars. John B. Hayes in Winchester, Virginia as well as Boswell in Chambersburg, PA are great stores though and well worth the trip. Since I got out of the army in 2004, I've only seen 3 other people smoking a pipe, and they were all in Frederick.
As far as urban pipe smokers, it's hard for an urban smoker of tobacco in general. More and more anti smoking legislation and ordinances, higher and higher taxes combine to push tobacco underground. With cancer sticks, it's easier. When pushed I could have a cigarette pulled out, lit, smoked, field stripped, and butt in the trash can in 4 minutes. Can't really do that with a pipe. And I'm sure there are pipe clubs around, but I've never gone looking for them. It's not why I smoke a pipe.