• smba-slider-chocolate.jpg
    • smba-slider-daffodil-(2)(1).jpg
    • smba-slider-sea-glass.jpg
  • March 7 - 8, 2020 

    The 2nd Annual St. Michaels ChocolateFest will be held the first weekend in March on Saturday, March 7th and Sunday, March 8th, 2020.    

    The St. Michaels ChocolateFest and will include restaurant chefs conjuring up amazing delectable special menu items to showcase chocolate inspired dishes and desserts.   Our inns and bed and breakfasts will feature chocolate inspired get-away packages.

    Chocolate lovers will enjoy strolling throughout the Town of St. Michaels to indulge in thousands of chocolate concoctions on Saturday, March 7th from 11:00 a.m. - 4:00 p.m. during the Chocolate Crawl, sampling amazing artisan chocolates, desserts, locally crafted wine, beer and spirits.  

    More information here.


  • Saturday, March 28, 2020

    The 3rd Annual Daffodil Days is scheduled on March 28, 2020 and is a celebration of over 25,000 daffodils planted throughout the town in 2017 with over 50,000 since then! 
    Our fabulous floral focused events will be held on Saturday throughout the Town of St. Michaels! Print your own Daffodil Map here or pick up a copy at Muskrat Park to do a self-guided tour! 
    Dress your pooch in a Daffodil theme! Best individual and best group will be judged. Register on Saturday at 10:45 a.m.in Muskrat Park. Judging at 11. Check out Business Window Contest, Historic Walking Tour at the St. Michaels Museum at 2 p.m. and free seed library at the library. See plein air painters from the St. Michaels Art League painting the array of daffodil beds with art sales from 2-3 p.m.
    More information here.

  • March 7 - 8, 2020  11am - 5pm

    Simpatico, Italy's Finest invites you to join them at their venue as part of the 2nd Annual St. Michaels ChocolateFest to enjoy tastings of hand-selected Italian wines, liqueurs and spirits specially paired with fabulous Italian chocolates and Italian cheeses under our heated tent and in the shop. You can learn about how to pair the various types of chocolates with wines, cheeses, and spirits.  Simpatico is a tasting venue for the ChocolateFest Crawl and also will be featuring many Italian wine-cheese-chocolate-liquor pairings on Saturday and Sunday.

    Simpatico is also the event location for the Chocolate Dessert Contest on Sunday, where you can try and vote for the best chocolate desserts.  

    More information here.


  • April 4 - 5, 2020

    The 9th annual Eastern Shore Sea Glass and Coastal Arts Festival in St. Michaels, Md. will be held on the beautiful waterfront location at the Chesapeake Bay Maritime Museum on Saturday, April 4, 2020 from 10–5 pm. and Sunday, April 5, 2020 from 10-4 pm.

    The 2020 Eastern Shore Sea Glass and Coastal Arts Festival will include over 80 artisans, educational lectures, live music, food, and libations.  Also scenic river boat tours can be taken for additional fee.

    More information here.


  • March 7th  Run/Walk starts at 9am

    Kick off your morning during ChocolateFest with a beautiful 5k (3.1 mile) run/walk and burn off those calories (so you can fill them back up with delicious CHOCOLATE!!!!) before heading in to town for all the festivities.

    The course will take you on the St Michaels Nature Trail, with a few minor road crossings. Participants will check in at TriCycle and Run, located at 929 S. Talbot Street, before heading over to the start area. 

    Packet pickup and registration begin at 8am, with the run/walk starting promptly at 9am. 

    Participants should park at the St Michaels Elementary School parking lot (100 Seymour Avenue, St Michaels, MD). 

    Awards will be given out for Overall Winners, as well as age groups. 

    Register and more information here.


  • April 25th - 26th  Noon - 5pm

    ​Winefest in St. Michaels is the premier international wine tasting event in Maryland, enjoy hundreds of domestic and international wines, delicious gourmet foods and a relaxing stroll through beautiful St. Michaels. Attendees will be able to "explore St Michaels" and visit the 10+ wine tasting venues throughout town.  These venues will be featuring more than 300 wines from around the world. Each wine venue will be retailing wine at special WineFest discount pricing. Stroll through town or ride the shuttle buses provided by WineFest.  Food will be available for purchase at most venues.

    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!


  • Classic Motor Museum

    The Classic Motor Museum includes excellent examples of Pre- and Post-WWII classic automobiles, mid-century muscle cars, vintage trucks, and motorcycles!  We moved a couple of cars out in July and August 2019.  Come by to see their replacements.  

    All ages can still enjoy our extensive collection of model cars and climbing aboard our 1931 American LaFrance fire truck. The pictured truck below remains in the exhibit barn, so come by to see it & hear the story "Chasing Grandpa".

    More information here.

  • Saturdays Through March 21st 10 am - 3 pm

    The crafts and creations of independent artists, hobbyists, crafters, and more are now at the St. Michaels Community Center from 10 – 3 p.m. each Saturday as part of the community center’s new From the Heart Mart.

    The indoor artisans market takes place at SMCC’s 103 Railroad Ave., and continues through Saturday, March 21, 2020.

    More information here.