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  • 10th Annual Italian Wine & Food Festival

    Saturday, October 12th

    Simpatico, Italy’s Finest celebrates Italian Wine, Food & Columbus Weekend with the 10th Annual “Simpatico Italian Wine & Food Festival at St. Michaels MD” of Italian Wine, Spirits, Liqueurs, Food, Music & Games on the Saturday of the Columbus Holiday weekend on October 12th from Noon to 5 PM. 

    The event will be held rain or shine in the tented lot “piazza” adjacent to Simpatico at 104 Railroad Ave.  Stop by and transport yourself to Italy!

    More information here.

  • OysterFest

    Saturday, October 26th

    Get ready to sip, slurp and savor at the Chesapeake Bay Maritime Museum's annual Oysterfest taking place on Saturday October 26th.

    CBMM’s OysterFest features oysters served a variety of ways, along with other local fare, craft beer, and spirits; live music on two stages, scenic river cruises aboard Winnie Estelle (weather dependent); an oyster stew competition; cooking presentations; Chesapeake Bay retriever and oystering demonstrations; children’s activities, and more.

    More information here.

  • Flavors of Fall at the Farmer's Market

    Saturday, October 19th

    Your favorite farm vendors will be serving fresh, fall inspired prepared foods from appetizers to desserts and everything in between. 
    Come join over 20 local farmers and vendors during our Flavors of Fall special event. 

    Regular market hours 8:30am to 11:30am
    Lunch 11:00am to 1:30pm

    More information here.


  • OysterJam

    Saturday, November 2nd

    OysterJam hosted by the Phillips Wharf Environmental Center will be held 12pm - 4pm on Saturday, November 2nd and will feature oysters from all over the state of Maryland giving you the opportunity to taste the differences between oysters grown in areas of the Bay and its estuaries.  Oysters will be offered raw, fried, steamed, in stew, and in signature dishes offered by select local restaurants.

    Oyster Jam will also play host to 7 craft breweries that will collectively offer 14 different beers for your tasting pleasure and feature live music with SouthBound.

    More information here.

  • Fall into St. Michaels

    Saturday & Sunday, October 19th - 20th

    The change of the season brings excitement and vibrant color to the town, as residents and businesses celebrate Fall into St. Michaels.  The annual pumpkin carving and pie baking contest will be held in the St. Michaels Community Center on Railroad Avenue.   All proceeds benefit the St. Michaels Community Center!   The annual Jack Russell races will continue on Sunday October 20th and the scarecrow contest is held throughout town with winners announced November 1st.

    More information here.

  • Tilghman Island Day

    Saturday, October 19th

    On Saturday, October 19th, 2019, from 10:00 a.m. until 7:00 p.m., the Tilghman Island Volunteer Fire Company will hold its annual Tilghman Island Day Celebration, known as “a visit to the home of the Seafood Industry.”
    Local watermen and other members of the community plan a number of exhibits and demonstrations designed to showcase the Chesapeake Bay waterman’s way of life throughout the day starting at 11 a.m.

    More information here.

  • Every Saturday 8:30 a.m. - 11:30 a.m.

    St. Michaels Farmers Market is a local, producer-only farmers market, operating Saturdays (April 13, 2019 - November 29, 2019) from 8:30 a.m.-11:30 a.m. RAIN OR SHINE. We are in the Public Parking lot - 204 S. Talbot Street) between Talbot and Fremont Streets, one block from the library in St. Michaels, MD.  ALL vendors can accept cash in addition to credit, debit and SNAP/EBT cards! 

    More information here.

  • Every Saturday 9:00 a.m. - 11:00 a.m.

    Take the car out of the garage and head over to the Classic Motor Museum for Cars & Coffee every Saturday! Coffee sponsored by Blue Heron Coffee.

    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 inns along with several larger full-service hotels.  Come and experience the beauty of St. Michaels and all this charming town has to offer!