Things To Do
St. Michaels, nicknamed “the town that fooled the British” after a clever lantern trick during the War of 1812, is a storybook Chesapeake harbor town full of sailboats, seafood, and cobblestone‑worthy charm. Just down the road, Tilghman Island is a tiny, working watermen’s village where boats slip out at sunrise, the Bay is always in view, and the whole place feels like a quiet, romantic escape at the edge of the water.
While you're in town, walk around, check out our favorite shops like Simpatico, The Christmas Shop, and Chesapeake Trading Company.
Check out a few of our favorite spots!
Muskrat Park
207 Willow Green Street, Saint Michaels, MD 21663
Our engagement spot right behind the church!
St. Michaels Winery
609 South Talbot Street, Saint Michaels, MD 21663, 410-745-0808
Pour a little happiness.
Eastern Shore Brewing
605 South Talbot Street, Saint Michaels, MD 21663, 410-714-1999
Grab A Pint! Cheers to beers by the bay.
LYON RUM // Windon Distilling Company
605 South Talbot Street, Saint Michaels, MD 21663, 443-333-9181
Raise a rum to romance.
St. Michaels Museum at St. Mary’s Square
201 East Chestnut Street, Saint Michaels, MD 21663, 410-745-9561
Local history museum in a 19th‑century home with walking tours that explain the town’s maritime past and architecture.
Chesapeake Bay Maritime Museum
213 North Talbot Street, Saint Michaels, MD 21663, 410-745-2916
Sam's favorite place in town. 18‑acre waterfront campus with historic boats, exhibits on Bay life, and boat rides.
Tilghman Watermen's Museum
6031 Tilghman Island Road, Tilghman Island, MD 21671, 410-886-1025
The Tilghman Watermen’s Museum celebrates, documents, preserves, and shares the history, traditions, heritage, and culture of Tilghman Island.
Classic Motor Museum of St. Michaels
102 East Marengo Street, Saint Michaels, MD 21663, 410-745-8979
For all the days along the way