Mark’s Score 8.3
When people think about visiting Maryland’s Eastern Shore, Princess Anne wouldn’t even be on the wish list. It is a place you pass through on your way to Chincoteague. At first blush, people aren’t wrong about that. It is true, a quick pass-through town will give you a sense of decay and decline. Somerset Ave. is full of boarded up, and ugly buildings. But if you take the time to stop and look around you will find a gem of a little town, steeped in history, and full of charm. The more I get to know Princess Anne, the more I have come to appreciate its charms.
Princess Anne was established in 1733 and named after the daughter of King George II. The town is located on the Manokin River. Because of its location on the river, it became a market town for the surrounding tobacco plantations. After the Civil War the town entered a protracted period of economic decline. Which in some ways is fortuitous, as a consequence of this decline many (approximately 300) historic structures have been preserved.
Princess Anne also has a very unique and quixotic historical footnote. A legend holds that after Emperor Napoleon I was defeated and banished to St Helena Island, Napoleon’s brother Jerome, who was married to Elizabeth Paterson of Baltimore, devised a plot to rescue Napoleon. Jerome and Nicholas Girod, the mayor of New Orleans (at the time), planned to steal Napoleon from St Helena and hide him at Beverly House in Princess Anne.
I freely admit that, for years, when I visited the Washington Inn for lunch or dinner, I would park on Somerset Ave, as close to the hotel as possible, dash in eat my meal and leave without giving the town further thought. I mistakenly thought there was nothing to see in Princess Anne. To me, it was just another clapped out rural village long past its use by date. Then one day, on a lunch run to Washington Inn, I parked on Prince William St in front of the library. And I thought to myself, “this is kind of pretty.” I was not in a hurry so I decided to take a closer look at Princess Anne.
I discovered that the town was chock-a-block full of beautiful and stately homes from the 18th and 19thcenturies situated along tree-lined streets. There is no need for rose colored glasses here, many of those homes are in a variety of states of decline and disrepair, but if you look past the peeling painted and unkempt yards, you can see the charm and beauty and the historical charm of the town.
Almost all the properties are privately owned, so you cannot see the interior of these stately houses. But there are a couple of exceptions, The Teackle Mansion Museum, the Washington Hotel, and St Andrew’s Episcopal Church. For those of you interested in old graveyards, some of the graves in the St Andrew’s graveyard date back to the early 1700s. If it is open, the interior of the church is worth a look.
Princess Anne is by no means a tourist destination. But if you are the type of person who likes to explore the path less travelled, Princess Anne well is worth a visit.
Places rated in or near Princess Anne
| Review Date | Place | Category | Score |
| 2024 Aug | Bordeleau Winery | Retail/Winery | 8.73 |
| 2025 May | Sugar Water | Restaurant | 8.56 |
Places reviewed in or near Princess Anne
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