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The trip through MD is so short that your odds of being caught are miniscule. New York is the problem. (It's a problem that could be solved if upstaters got their wish, and everything north of Rockland and Westchester counties was split off into a different state.)

On my only (so far) trip to New England, I was driving our huge honkin' Razorback Red full-size conversion van, pulling a 24' travel trailer, with Texas plates on both. I had a dozen or so guns in the trailer, and several thousand rounds of ammo (we were going to Porcfest in NH, and liberty-lovers love to shoot!)

Because I am covered under LEOSA, I was also carrying a concealed handgun during the whole trip, including MD, NY, CT, and MA. Even with my credentials I had some worries about those states, and I definitely wouldn't recommend carrying in those states for unlicensed non-LEOs. I knew that even if I had gotten thrown in jail, I'd beat the charge; Joe CHL won't beat it, and could become a felon depending on the state.