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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!

  • WineFest at St. Michaels

    April 29 - 30

    WineFest at St. Michaels is a wine festival like no other.   Enjoy the beauty of St. Michaels as you "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. 

    Noon - 5 pm daily

    More information here.

  • St. Michaels Running Festival

    May 20

    The St. Michaels Running Festival, now celebrating our 6th year, is one of the premier destination races in the Mid-Atlantic. Held in one of the oldest waterfront towns on the Chesapeake, St. Michaels and the Bay Hundred runners will be treated to beautiful farm lands, gorgeous water views and a rockin' after-party in downtown St. Michaels.   

    Not running? Come cheer on the runners/walkers then head into town to eat, shop, play and stay!

    This event is Rain or Shine.

    More information here.

  • St. Michaels Brewfest 

    June 3 

    St. Michaels Brewfest is held Saturday, June 3rd between three locations in St. Michaels, all within a very short walk of each other. Held in three locations, from the Historic Mill District to two locations on the water, at Foxy's Harbor Grille and The Crab Claw, held right on the water. You will get to see this charming town while drinking some of the best beers the region has to offer.  

    Limited VIP tickets for the BrewMaster Cruise on the Patriot Boat Cruises leaving Saturday at 10:45 a.m. also available.

    More information here.