• 314.jpg
  • 50 Free Things to do in St. Michaels

  • St. Michaels offers a wonderful quiet charm, peaceful haven for a day, weekend or vacation.  Stroll the historic streets where lovingly restored homes welcome you to take a step back in time. Historic sites, enchanting Inns, Bed & Breakfasts and Museums give you the feeling of what was once a thriving Colonial village and is now home to many who are a bit resistant to the hustle and bustle of modern life.

    Just a leisurely drive from Baltimore, Washington and Philadelphia, St. Michaels not only offers a quiet escape, but don’t be surprised if we keep you busy (if you want to be.)


    While shopping and dining are very popular pastimes, the beautiful Miles River and St. Michaels Harbor offers boaters and sailors and those who just like to be near the water, the perfect destination. 
    For the serious sportsman, excellent fishing and guided hunting make St. Michaels a year-round getaway. Cycling enthusiasts find St. Michaels a must-stop on their itinerary, the flat roads and scenic by-ways make the Bay Hundred Area a great cycling route.

    Geocaching is also a wonderful way to explore St. Michaels and the Bay Hundred Area, to find out more about geocaching in the area, visit the Chesapeake Conservancy website.

    Many fine restaurants, lovely places to stay and interesting shops add to the ambience, making St. Michaels a visitor’s delight.


    The historic town of St Michaels dates back to the mid-1600s when it served as a trading post for area tobacco farmers and trappers. In 1677 the Christ Episcopal Church of St Michael Archangel parish was founded in present day St. Michaels. In 1778 a British land agent, James Braddock, purchased 20 acres and deeded 58 lots. This created St. Mary's Square, the historic center of St. Michaels. To this day, this charming seaside resort town reflects its colonial past, as many of the area's homes date from the late 1700s to the late 1800s. 

  • 1.         Learn about the War of 1812

    2.         Visit one of the oldest Episcopal Churches in the country

    3.         Enjoy live summertime music in Muskrat Park

    4.         Kiss on Honeymoon Bridge

    5.         Walk Frederick Douglass’ path to freedom

    6.         Explore the region that inspired Michener’s Chesapeake

    7.         Sit along the harbor and bird watch

    8.         Bring your camera, St. Michaels is a great place to sharpen your skills

    9.         Walk along the side streets and step back in time

    10.       Watch our beautiful skipjacks under sail

    11.       Find a secret beach

    12.       Take an Art Walk tour of our galleries

    13.       Catch a sunrise at Muskrat park.

    14.       Tour a distillery

    15.       Tour a brewery

    16.       Shuck an oyster

    17.       Discover one-of-a-kind antiques

    18.       Watch shopping carts race at midnight on St. Patrick’s Day

    19.       See the locals compete at the Wednesday night sailboat races

    20.       Visit during Fall into St. Michaels festivities and pumpkin carving contest

    21.       Check out cool gingerbread houses during Christmas in St. Michaels

    22.       Watch our historic log canoes race on the Miles River

    23.       Stroll and shop for unique gifts, clothing and jewelry

    24.       Chicken-neck for Chesapeake blue crabs

    25.       St. Michaels is pet friendly, so bring your pooch, too!

  • 26.      Geocaching along the historic Bay Hundred Area

    27.     Ride your bike or jog along our Nature Trail

    28.      Tour historic homes decked out for the holidays

    29.       Watch a sunset over the Eastern Bay

    30.       Kayak or canoe along hundreds of miles of shoreline

    31.       Spy osprey and blue heron in their nests

    32.       Visit Phillips Wharf Environmental Center in Tilghman

    33.       Drink eggnog on the porch during the Christmas Parade

    34.       Learn to needlepoint

    35.       Watch the 4th of July Fireworks

    36.       Relax in Muskrat Park and take in the harbor views

    37.       Visit the Farmer’s Market on Saturday mornings

    38.       Watch the Maryland State Champion High School baseball team

    39.       Visit an art gallery

    40.       Watch an artist “Paint the Town”

    41.       See where they filmed Wedding Crashers

    42.       Bike to Tilghman Island

    43.       People watch!

    44.       Have a picnic along the water in Hollis or Muskrat Park

    45.       Enjoy a local musicians playing at various locations year round

    46.       Learn about Chesapeake Bay history at the various museums

    47.       Meet a local and hear their story

    48.       Listen to the church bells

    49.       Fall in love...

    50.       Fall in love with St. Michaels!!!

  • Before You Visit:

  • St. Michaels, Tilghman and the Bay Hundred area have a wide range of lodging options to suit every taste and budget. Find the perfect place to fit your needs here.

  • Nothing says Chesapeake Bay like a steaming pile of locally caught Maryland blue crabs, and our restaurants are serving the Chesapeake Bay's bounty, from steamed crabs and crab cakes to sweet soft shell clams and fresh rockfish.  Find the perfect restaurant here.

  • St. Michaels offers shopping galore, with an eclectic range of shops, including jewelry, clothing and home decor, galleries and more!   Stop by one of the many tasting rooms, offering specialty foods and locally made libations. Find our unique shops here.

  • Whether you're an experienced kayaker, a day-tripping boater, a sailing novice, a history buff, an avid fisherman, or anyone else who yearns to spend some time on the water, you will find something to do in St. Michaels and Tilghman Island. It's time to get out on the water and enjoy the outdoors!  Find your boating options here.

  • Special thanks to William Wilhelm Photography, Charles Riter Photography, the Town of St. Michaels and the Chesapeake Bay Maritime Museum for the use of their photos.

© Copyright 2017 St. Michaels Maryland Business Association. All Rights Reserved. Site provided by MicroNet - powered by ChamberMaster software.