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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!

  • Fall into St. Michaels

    October 20 - 21, 2018 

    The annual Fall into St. Michaels event features participating local businesses  in the highly anticipated pumpkin carving & scarecrow contests and the professional and home baker pie baking contests which 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! 

    More information here.

  • Tilghman Island Day

    October 20  10:00 a.m. - 5:00 p.m.

    Annual Tilghman Island Day on October 20, 2018.  Enjoy live music, fresh seafood, boat docking contest and races. Fun for the family! 

    Benefits the Tilghman Island Fire Department.

    More information here.

  • Jack Russell Races

    October 21, 2018  11:00 race start time

    The St. Michaels Inn will host the annual Jack Russell Races beginning at 11:00 am. Registration is available online and at 10 a.m. that morning.

    The event will be held, rain or shine! Refreshments, including Coffee & Donuts and a Bloody Mary & Mimosa Bar, will be available on site. There will be live raffles of items from area restaurants and retailers between races!

    The proceeds from the benefit will go to St. Michaels Community Food Bank and Humane of Talbot, Caroline and Dorchester Counties.

    More information & to register your dog here.

  • St. Michaels Farmers Market

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

    St. Michaels Farmers Market is a local, producer-only farmers market, operating Saturdays (April 14th-November 17, 2018) 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.

  • OysterFest

    October 27, 2018 10:00 a.m. - 5:00 p.m.

    OysterFest is a celebration of the Chesapeake’s oyster and this year also means the relaunch of the 1889 bugeye Edna E. Lockwood with her new log-hull bottom.

    The event features live music on two stages, boat rides, retriever demonstrations, oysters and other local fare, and oyster stew competition and cooking demonstrations, along with children’s activities, oyster demonstrations, harvesting displays and Chesapeake-related documentary screenings.

    More information here.

  • Wine Cellarbration

    October 27, 2018  Noon - 6:00 p.m.

    Wine Cellarbration, a special Fall WineFest at St. Michaels event will be held one day on October 27th, 2018. Offering both a regular ticket which provides tastings of 40-60 wines and a VIP ticket.

    We will be tasting a group of carefully selected wines which have been chosen to offer wines for everyone: sparkling, whites, rose, reds, and dessert wines. If you know Winefest and its 10-year history, you know these wines will have global appeal. The list will include both domestic and international varietals both in regular and VIP venues.

    More information and tickets here.




  • SHOP

    St. Michaels offers an eclectic range of boutique shops offering specialty foodsjewelry, clothing and home decor as well as galleries throughout the town. Shopping along our charming streets you'll find some fun items to commemorate your visit or to give to someone special upon your return home. Our boutique clothing stores, feature everything from cocktail attire to casual weekend wear to trendy nautical fashions, and accessorize your new outfits by browsing our many artisan & estate jewelry stores.

    Learn more here.

  • EAT

    St. Michaels is renowned for their Chesapeake Bay cuisine featuring locally caught fish, crabs and oysters, but our diverse eateries offer much more than that!  You’ll find Italian, Irish, Southern inspired restaurants, too.  The restaurants throughout St. Michaels, Tilghman and the Bay Hundred area offer amazing selections for breakfast, lunch and exceptional dinner experience.  We also offer many waterfront dining options, from the casual crab house to an elegant five course meal.   

    Learn more here.  

  • PLAY

    St. Michaels offers everything for its visitors, from self-guided historical walking tours, unique shopping in our boutiques and galleries, exploring our museums, kayaking and biking along the many Bay Hundred scenic byways, charter a fishing trip or just relaxing along the water’s edge, you’ll find St. Michaels, Tilghman and the Bay Hundred area has something for everyone.  

    The Bay Hundred area is surrounded by water, so you’ll want to get out on the water during your visit and experience our beautiful harbor town and Chesapeake Bay tributaries.

    Learn more here.

  • STAY

    St. Michaels, Tilghman and the Bay Hundred area have a wide range of lodging options to suit every taste and budget. There are many accommodations to choose from, including elegant full-service inns, charming bed-and-breakfasts, and delightful cottage vacation rentals.  

    Our bed-and-breakfasts and inns are a staple of the St. Michaels area, and many are located in the heart of St. Michaels; where you are within a leisurely walking distance to the town’s shopping, dining, museums and boating excursions. 

    Learn more here.

  • We're a Dog Friendly town!

    Did you know St. Michaels is a dog friendly town? Many of our lodging, shops and restaurants are dog friendly!  Check out our website and contact any businesses you would like to visit. 

    Looking to do something fun with your pint sized pooch?  

    Check out the annual Jack Russell Races during our Fall into St. Michaels event. 

    The races will be held Sunday, October 21st!



  • Cars & Coffee

    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.