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  • The change of the season brings excitement and vibrant color to the Town of St. Michaels, as residents and businesses celebrate their annual festival Fall into St. Michaels, Jack Russell Races on Sunday and the new Wag-O-Ween event on Saturday.   

    Enjoy our fabulous restaurants, charming boutiques and galleries, or take a boat ride out on the water for some local history and sights.    Stay in our inns and B & B's for some much needed relaxation. The autumn months are a perfect time to visit St. Michaels for a romantic retreat or a family get away. 

    More information here.

  • The Chesapeake Bay Maritime Museum hosts Mid-Atlantic Small Craft Festival XXXX on Friday-Sunday, Oct. 6-8, welcoming one of the nation’s largest gatherings of small boat enthusiasts and unique watercraft back to its waterfront campus.


    Hundreds of amateur and professional boatbuilders and enthusiasts will come from all over the region to display their one-of-a-kind kayaks, canoes, and other traditional small craft at the 40th edition of the annual festival, which runs 10am–5pm all three days.


    Tickets and more information here.

  • Get ready to sip, slurp, and savor at the Chesapeake Bay’s favorite fall festival! 

    The event features live music on two stages, boat rides, retriever demonstrations, oysters for purchase from fried to raw and everything in between, you can also sign up to be in the coveted oyster eating contest!  Shop local vendors while listening to the  sounds of local bands. 

    Tickets and 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!