Port Tobacco had been the second largest river port in Maryland—St. Mary’s City was the largest at the start of the Colonial Era. Ships from Europe brought prized goods to the Port and left with the much coveted "evil weed" - tobacco. Over time, due to poor farm planning, or rather over farming, the harbor gradually silted up and the river trade declined. The final blow to Port Tobacco came with the burning of the courthouse in 1892 at which point the county seat was moved to nearby La Plata.
With the lure of the beautiful area homeowners gradually have brought some vibrancy back to the area and historic preservation efforts are strong. Must see sites include St. Ignatious Chruch - the oldest Catholic parish in the US which commands the high ground overlooking the confluence of the Tobacco and Potomac Rivers - one of the best views in the state I have to add. The orginal brick court house stands not far from a charming one room school house and tobacco barns dot the rolling landscape.
The most exciting visit for me personally was our trip to Thomas Stone National Historic Site just a few miles from Port Tobacco. It was here that Thomas Stone had built a prosperous farm before becoming important enough on the polictical scene to be one of the signers of the Declaration of Independence - he literally wrote himself into American history. We found ourselves alone on 322 acres of revolutionary history. The plantion is was named Haberdeventure by the Stones - a “dwelling place in the winds”. Purchased in 1770 by Thomas Stone, this restored plantation home has been open to the public as a National Historic Site since 1997. I found the out buildings especially pleasing - well kept but dating back to the mid-19th Century, they suited the landscape perfectly. The house is modest in scale and well proportioned with a generous balcony to oversee the land. The family plot is nearby and seems a spledid resting place, Thomas Stone is buried here as well . The only horror story here was the mosquito's - we all managed to get countless bites, so bring along repellent!
We capped a perfect day with carry out from a local BBQ institution - Johnny Boys Ribs, located at 7540 Crain Hwy, La Plata, MD. This place is well known locally and even regionally. Don't let the modest roadside architecture prompt you pass this treat up. You will exprience family type finger licking good Bar B Que. All of the salads are homemade and they have a secret BBQ receipe that pulls in hungry crowds who patiently que up for this treat.
You can reach Port Tobacco in about an hours time once you pick up Rte 5 right off the Beltway and turn on 301 south in the direction Upper Marlboro and La Plata. Unless you're headed here specifically there's really no reason to pass through because this is the end of the road in Charles County.
This is also the route to take if you're interested in the Assasination Plot of President Lincoln and Booths post assissination escape attempt. If you follow the roads mentioned above you'll pass turn offs for Surrats Tavern, Dr. Mudd's House, not to mention Port Tobacco itself where this nefarious scheme was hatched at a local hotel / inn.
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