Things to Do in St. Michaels, MD


I’m visiting St. Michaels and Tilghman Island on Maryland’s Eastern shore in a few short weeks and am planning my itinerary. There are quite a few things to do in St. Michaels, Maryland, especially if you enjoy nature and are interested in the history of the area. Here is what we have planned:

Day One – Arrival in St. Michaels

There are a number of wonderful resort and luxury hotel options in the area, as well as some beautiful bed and breakfasts. We opted for a more economic option on this trip and will be staying at St. Michaels Inn.

Once we check in, we will be exploring St. Michaels a bit, especially the shops of Talbot Street and then heading back for dinner at T at the General Store. (Did I mention I have a thing for tea? I am so excited about their tea filled menu!!)

Day Two – Visiting St. Michaels

Chesapeake Bay Maritime Museum is the must visit spot here. We originally planned to include a Miles River cruise on the Winnie Estelle. Unfortunately, she is not currently available. If we can get our times to line up, we will book a cruise on the Patriot instead. This would also be a great time to take a ferry to Oxford to explore this historic fishing village.

In the afternoon, we plan to visit St. Michaels Winery and then wander back through town in time to hit Theos for dinner.

Day Three – Tilghman Island

We have a lot we want to do on Tilghman Island. I debated about adding a fourth day to our trip and may still do so if we don’t get to everything. We want to find Phillips Wharf, the nature center beside Knapp’s Island drawbridge, the Tilghman Waterman’s Museum and the local bookstore. After absorbing all that knowledge, we plan to visit Two if By Sea for a latish lunch and then try to head out to Black Walnut Point.

Then, it will be off for home.

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