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!!!