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  • Visiting St. Michaels in the Winter is a tradition for many, from anniversary celebrations to just wanting to get away and unwind.   Our quaint shops, world-class dining and relaxing small town vibe helps to beat those winter blues.

    Enjoy our cozy bed and breakfasts, inns and vacation rentals in and around St. Michaels for a romantic get away.  

    Book your stay here.

  • The 6th Annual St. Michaels ChocolateFest will be held March 2, 2024 and will include restaurant chefs conjuring up amazing delectable special menu items to showcase chocolate inspired dishes and desserts.  The Chocolate Crawl will take place on Saturday, March 2, 2024 from 11:00 a.m. - 4:00 p.m. until sold out throughout the Town of St. Michaels at participating businesses and restaurants.  Chocolate lovers will enjoy shopping throughout town sampling amazing artisan chocolates, desserts, wine, beer and spirits.

    More information here.

  • The Eastern Shore Sea Glass and Coastal Arts Festival will be held Saturday, April 20th and Sunday April 21, 2024 at the Chesapeake Bay Maritime Museum in St. Michaels, Maryland.

    A fun-filled tradition since 2010, the Eastern Shore Sea Glass & Coastal Arts Festival highlights artisans and craftspeople who come from near and far to exhibit and sell coastal and sea-glass related jewelry, home décor, art, and more.   

    More information here.

  • About 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 B&B's, award winning inns and full-service hotels to welcome you!

    Come and experience the beauty of St. Michaels and all this charming town has to offer!  See You soon!