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  • Welcome to St. Michaels & the Bay Hundred Area

    St. Michaels is a picturesque harbor on Maryland's Eastern Shore and was named as one of the Top 10 Best Small Coastal Towns in America by USA Today.  Its harbor and some homes date back to the mid-1600's, and is home to the Chesapeake Bay Maritime Museum where you can immerse yourself in our maritime history.   The St. Michaels area is perfect for outdoor activities including sailing on historic Skipjacks, kayaking, golfing and bicycling.  St. Michaels is also known for exceptional restaurants, from quaint romantic bistros to waterfront restaurants, serving fresh seafood including the best tasting crab cakes!  For shoppers, you will find an eclectic range of boutique shops offering specialty foods, jewelry, clothing, home decor and art galleries throughout the town.  For overnight lodging, we have many small inns along with several larger full-service hotels.  Come and experience the beauty of St. Michaels and all this charming town has to offer!

  • Columbus Day Wine Festival at Simpatico

    October 14 -15

    Simpatico, Italy's Finest celebrates Columbus Day with the 8th Annual "Columbus WineFest at St. Michaels," featuring Italian Wine, Food, Art & Games, on Saturday, October 14th & 15th 2017 from Noon to 5 PM.  

    Christopher Columbus will be in attendance and will share tales of his exploration adventures as part of the festivities planned for adults and children of all ages! The event will be held rain or shine in the tented lot adjacent to Simpatico. Stop by and transport yourself to Italy! Ciao!

    More information here.


  • Fall into St. Michaels

    October 21-22 

    Fall is the time when we yearn for snuggling in sweaters, we gear up for pumpkin patches and we sip on apple cider. The autumn months are a perfect time to visit St. Michaels for a romantic retreat or a family get away.  
    The annual pumpkin carving, pie baking contest and scarecrow contest will be held in the St. Michaels Community Center on Railroad Avenue.   Stop by at vote for all your favorites, then grab a slice or two of pie, all proceeds benefit the St. Michaels Community Center!
    Jack Russell Races on Sunday will take place at the Inn at Perry Cabin front lawn at 11:00 a.m.

    More information here.

  • OysterFest 

    Saturday, October 28

    OysterFest, a celebration of the Chesapeake’s favorite bivalve, will return to the Chesapeake Bay Maritime Museum on Saturday, Oct. 28, 2017.

    The event features live music, an oyster stew competition, boat rides, retriever demonstrations, oysters and other local fare, and cooking demonstrations, along with children’s activities, oystering demonstrations, harvesting displays, and more.  

    St. Michaels restaurants also showcase the tasty bivalve all weekend long. 

    More information here.