After exploring Oxford, we continued up the eastern shore of Maryland to St. Michaels. The 31.5 mile trip took us about 6 hours and we dropped anchor in the Miles River on the outskirts of the anchorage area. The next morning it was time to explore the town.

St. Michaels is a quaint historic town with lots of shops, inns and bed & breakfasts and popular restaurants lining its beautiful harbor. It makes sense that it was named one of USA Today’s Top 10 Best Small Coastal Towns and Coastal Living Magazine‘s Top Ten Romantic Escapes in the USA.

Named after the Episcopal Parish that established itself there in 1677, the town attracted settlers who engaged in tobacco growing and shipbuilding. As shipbuilding declined, a new industry of oystering took its place and the area known as Navy Point became a site of seafood packing houses, docks, and work boats. The Chesapeake Bay Maritime Museum now occupies this land with its large collection of Bay boats, interactive exhibits and 35 buildings that are part of its campus.

Our first order of business was to locate a place to pick up some some fresh produce. There aren’t a lot of groceries within walking distance, but we managed to find a small market so we set off in the dinghy with Sophie. We located the free dinghy dock next to the Crab Claw restaurant and were immediately impressed with the docks and waterfront. There were lots of shade trees, grass, benches and picnic tables. Signs around the area noted important or historical buildings and landmarks. We walked along the waterfront that took us over a small bridge and spotted a mama duck with her 3 ducklings. We continued on toward town and walked past lots of shops and restaurants. On our way to the market shop, we passed a winery, brewery and rum distiller, all right next to each other (Sampling from all three in one afternoon could be dangerous!). We came back later in the afternoon to visit Eastern Shores Brewery to sample some of the local beer. Eastern Shores Brewery is the oldest brewery on Maryland’s eastern shore. The beers were excellent, but the reason we came back the next day was that they were dog friendly indoors with excellent air conditioning. With it being so hot in the late afternoons, it was a nice reprieve to get to sit inside with AC and have Sophie with us.

We spent two days in St. Michaels and one of those mornings we decided to check out the Chesapeake Bay Maritime Museum. As mentioned above, it’s quite a collection of floating boats, a working shipyard, exhibits and lots of buildings that make up its campus. We were impressed by the sheer size and number of exhibits offered. We got to check out the Hooper Strait Lighthouse and stair-climb to the top for a beautiful view of the harbor. We explored numerous boats and exhibits that show the history of the Chesapeake Bay and the way of life and work through the years. Buildings or exhibits focused on everything from birding, oystering, crabbing, recreational boating to Naval history. It was quite an exhaustive collection and was well worth the trip.

We really enjoyed St. Michaels and would definitely visit again. It’s such a cute town with so much to offer to any visitor.

Oxford, MD to St. Michaels, MD = 31.5 nm

TOTAL miles to date: = 1,501 nm