- Visit one of the oldest Episcopal Churches in the country
- Enjoy live summertime music on Thursday's in Muskrat Park
- Kiss on Honeymoon Bridge
- Walk Frederick Douglass’ path to freedom
- Explore the region that inspired Michener’s Chesapeake
- See the Inn at Perry Cabin from the wedding scene of Wedding Crashers
- 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
- Watch our historic log canoes race on the Miles River
- Stroll and shop for unique gifts
- Ride your bike or jog along our Nature Trail
- Tour historic homes decked out for the holidays
- 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
- Watch the 4th of July Fireworks
- Relax in Muskrat Park and take in the harbor views
- Visit the Farmer’s Market on Saturday mornings
- Visit an art gallery
- Ride the Oxford/St. Michaels Bike Trail
- Play in a park
- Listen to the church bells