
- Watch a reenactment of the War of 1812
- Visit one of the oldest Episcopal Churches in the country
- Enjoy live summertime music in Muskrat Park
- Kiss on Honeymoon Bridge
- Walk Frederick Douglass’ path to freedom
- Explore the region that inspired Michener’s Chesapeake
- Watch a little league game at Perry Cabin Ball Field
- See the Inn from the wedding scene of Wedding Crashers
- Tell Santa what you want after the Christmas Parade
- Watch our beautiful skipjacks under sail
- Trick or treat on Chestnut Street
- Tip toe through our historic cemeteries
- Find a secret beach
- Tour a winery
- Tour a brewery
- Tour a distillery
- Shuck an oyster
- Discover one-of-a-kind antiques
- Watch shopping carts race at midnight on St. Patrick’s Day
- See the locals compete at the Wednesday night sailboat races
- Make a scary costume and join the Halloween Parade
- Check out cool gingerbread houses during Christmas in St. Michaels
- Watch our historic log canoes race on the Miles River
- Stroll and shop for unique gifts
- Chicken-neck for Chesapeake blue crabs
- Pant and wag your tail when “St. Michaels Goes to the Dogs”
- Race your Jack Russell Terrier for charity
- Ride your bike or jog along our Nature Trail
- Tour historic homes decked out for the holidays
- Watch a sunset over the Eastern Bay
- Kayak or canoe along hundreds of miles of shoreline
- Spy osprey and blue heron in their nests
- Drink eggnog on the porch during the Christmas Parade
- Learn to needlepoint
- Watch the 4th of July Fireworks
- Relax in Muskrat Park and take in the harbor views
- Visit the Farmer’s Market on Saturday mornings
- Watch the Maryland State Champion High School baseball team
- Visit an art gallery
- Watch an artist “Paint the Town”
- Ride the Oxford/St. Michaels Bike Trail
- Row four St. Michaels Water Trails
- People watch!
- Climb aboard a pirate ship
- Feed the ducks at Hollis Park
- Play in a park
- Meet a local and hear their story
- Listen to the church bells
- Fall in love
- Fall in love with St. Michaels!!!