Though its picturesque setting earned national attention as the backdrop for the movie Wedding Crashers, St. Michaels’ physical beauty offers only a glimpse of its idyllic charm. Nestled along the Miles River in the heart of the Chesapeake, the historic waterfront town provides itineraries for trips of all kinds, from romantic getaways to family vacations. Home to museums and boutiques, gourmet restaurants and crab shacks, and plenty of adventure by land or by sea, foodies, sailors, wine connoisseurs and art enthusiasts alike can get lost in all the town has to offer.
Early one morning in August 1813, British barges floated up the Miles River and planned an attack on St. Michaels. But the local militia mounted a spirited defense, blocking the harbor and repelling the world’s most feared naval forces. These rich and entertaining pieces of history are alive and well in St. Michaels, where the town’s story is waiting to be told. Discover instrumental people in the town’s history at the St. Michaels Museum and explore the critical role of the skipjack at Chesapeake Bay Maritime Museum. Learn about the significance of historical landmarks on a historic walking tour.
Shop boutiques, browse antiques, and indulge in homemade ice cream on Talbot Street. Rent bicycles or a scooter and let the wind be your guide. Find your inner artist at one of the many galleries. Pick Chesapeake Bay blue crabs. Partake in a tour and a tasting at the town’s winery, brewery or distillery—the perfect prelude to the culinary tour: a delicious meal at one of many award-winning restaurants. Choose a quiet weekend to explore the town on your own, or be inspired by energy of other visitors by planning your trip around one of the many lively town-wide events.
If your idea of enjoying the great outdoors is sitting on a patio with a refreshing cocktail in hand, St. Michaels can deliver. But if you want to soak up the sun, hit the trails, or get out on the water, you won’t be disappointed either. In addition to four beautiful parks and miles of trails for biking, St. Michaels’ seemingly endless shoreline offers visitors a chance to get a duck’s eye view. Rent a standup paddleboard, a kayak, a canoe, even a boat or a jet ski. Get your work out on, or relax: sail the day away or take a sunset cruise. The nautical choice is yours.
This beloved destination is continuously mentioned on national lists as a top destination for shopping, food, and most beautiful small towns in America. Situated beside the Miles River, step back into 19th century ambience, but with 21st century conveniences, and while the hours away in the unique shops, indulge in steamed crabs, and get out on the water. Create your own experience with these offerings from St. Michaels.