Nestled along the Miles River, St. Michaels is a historic waterfront town that’s home to museums and boutiques, gourmet restaurants and crab shacks, and plenty of adventure by land or by sea.
Dive into History
The Chesapeake Bay Maritime Museum sits on an 18-acre park-like, waterfront campus and includes a stunning new interpretive welcome center. Numerous indoor and outdoor exhibits, including a screwpile lighthouse, working shipyard, and floating fleet of historic vessels unveil the story of the region and its people. If visiting on a weekend, sign up for a one-hour highlight tour for a more personal experience and deeper historical dive, or get out on the water with a 45-minute Harbor Highlights cruise when in season.
The St. Michaels Museum at St. Mary’s Square, open seasonally, includes permanent exhibits on St. Michaels: Life Over Time, Frederick Douglass, and the Chaney House, built by the free, Black Chaney brothers in 1851. It also offers a self guided walking tour of St. Michaels. Baseball Hall of Famer Harold Baines got his start at St. Michaels High School before embarking on his 22-year career in major league baseball.
Shop Local
Avid shoppers will rejoice on Talbot Street, as a collection of independently owned shops and boutiques showcase jewelry, home furnishings, and housewares. There’s even a two-story feel-good spot for holiday décor and ornaments that’s open all year long.
Lift a Glass
Sample wine, beer, and spirits at a trio of tasting rooms within steps of one another. St. Michaels Winery, Eastern Shore Brewing, the Eastern Shore’s oldest brewery, and LYON RUM maker Windon Distilling all create their magic right on site.
Get on the Water
You can take a boat ride aboard many vessels, including the Patriot, a two-story steamship replica renowned for its historic and wildlife tours. Sail aboard the H.M. Krentz, a rare vintage skipjack, or enjoy a romantic sunset cruise on Selina II, a yacht operated by the owner-guide. If you’re seeking a more social experience, check out one of the communal boat tours offered by the St. Michaels Harbor Shuttle or utilize their water taxi service to hop from location to location. If you’d rather self-propel, you can rent a kayak, paddleboard, or canoe to traverse the waterways on your own.
Eat Well
Fresh seafood is plentiful, and many restaurants offer views of the majestic Miles River. Crack open a Maryland blue crab and experience the traditional Eastern Shore dining experience. Cozy up in a romantic setting and show your loved one a meal to remember. In town, you can sample cuisine from around the world, enjoy a buzzy local favorite known for its wood-fired pizzas, or try out a nautical-chic outpost serving specialties like spicy Galician anchovy toast. Come morning, grab fair trade coffee and colorful acai bowls, or for a heartier breakfast, enjoy the big pancakes at a local’s favorite saloon.
Relax in a Room with a View
St. Michaels is synonymous with relaxing luxury. An evening here allows you to rest your head in a short-term rental, historic inn, marina-front room, or world-renowned resort. St. Michaels is home to one of the world’s most luxurious properties, Inn at Perry Cabin, where you can book a spa treatment, soak in the pool, play tennis and golf, take a boat ride, or borrow a bike to explore the town.
