St Michaels, Maryland: a 2-day Weekend Itinenary    

St. Michaels was once a Colonial village known for oystering and shipbuilding. This charming town is located along Maryland’s Eastern Shore. Due to its idyllic location, there are unique waterfront restaurants and shops, plus activities like sailing, kayaking, fishing, and more. As a visitor, there is plenty to see and do, regardless of the season.

Popular attractions to see on your day trip include visiting history museums, the 1879 Hooper Strait Lighthouse, an iron mill, a local rum distillery, and many delightful seafood restaurants and markets.

Our recommended 2-day itinerary at a glance:

Day 1:
• The evening before, check into The Inn at Perry Cabin, our local favorite place to stay in the area. There is great breakfast served in the morning. The Wildset is another good option.
• After breakfast, visit Chesapeake Bay Maritime Museum which portrays what life was like from the time of sailboats, the steamboat era, to the advent of gas-powered engines.
• Have lunch at Bistro St. Michaels which features American food prepared with European style and techniques. The chef sources local and high-quality ingredients, including sustainable seafood, free-range eggs, and organic vegetables.
• In the afternoon, visit St. Michael's Museum to learn about the area history. You can participate in a guided walking tour or tour the exhibits that were curated by museum staff.
• In the evening, have a romantic dinner at Chesapeake Landing or indulge in great eats at 208 Talbot.

Day 2:
• On the second day of your trip to St Michaels, take a relaxing cruise down the Miles River with Patriot Cruises. The 75-minute-long scenic tour will let you see many gorgeous locations of St. Michaels’ Eastern Shore from stunning 200-year-old mansions to filming locations of the Wedding Crashers.
• In the afternoon, enjoy wine tasting at St. Michaels Winery followed by dinner at Foxy's Harbor Grille.
• End your day with a romantic dinner at St. Michaels Crab and Steak House located in a 1830s building that was formerly an oyster shucking shed. Given its location to the sea, many of the items available on the menu are Eastern Shore seafood specialties.

St Michaels, Maryland is 1 hr 35 min (78.8 miles via US-50 E) from D.C.:

Map:

Some more ideas for your St Michaels trip: