Events on Maryland’s Eastern Shore

Find upcoming events on Maryland’s Eastern Shore, including festivals, live music, arts and culture, food and drink events, and seasonal celebrations. This local events calendar highlights what’s happening in Easton, St. Michaels, Oxford, Chestertown, and nearby Eastern Shore towns, making it easy for visitors and residents to plan their time in the area.

Looking for events near your rental? Browse vacation rentals by town.

Ongoing

Sip | Savor | Shop

Immerse yourself in the enchanting flavors and cultural richness of Greece at our monthly Greek food experience! Discover an enticing assortment of cheeses, ranging from creamy feta and Manouri, to […]

Cambridge Traditional Crab Run

We are excited to say that we are returning for our traditional Sunday (Mother's Day) event!!! The Crab Run consists of a half marathon (13.1 miles) immediately followed by a […]

Mimosas for Mommy in St. Michaels

Celebrate Mom in Style at The Galley Restaurant! Treat Mom to an unforgettable Mother's Day experience at our 4th Annual Mimosas for Mommy Celebration! Indulge in a relaxing brunch that […]

Mother’s Day Sip & Paint in Easton

Looking to spend some quality time with Mom this Mother's Day? Well, look no further. Far Eastern Shore Winery will be hosting our 3rd Annual Mother's Day Sip & Paint […]