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.
Celebrate the 20th anniversary of Chesapeake Bay Week with a special film festival, presented by CBMM in collaboration with Maryland Public Television. Dive deep into the Bay's rich history through the inspiring stories of the people who call it home. Throughout this three-day preview event, enjoy advanced screenings alongside panel discussions and expert talks, as […]
Vintage Family Farms and Corah's Corner are teaming up again to bring you a create your own Tulip bouquet bar with our own field grown Tulips and your favorite Tequila […]
The Eastern Shore Sea Glass and Coastal Arts Festival brings artisans and craftspeople who will exhibit and sell coastal and sea-glass related jewelry, home décor, art, and more. The popular […]
Event by Big Mack’s Kitchen Venue Eastern Shore Brewing https://www.facebook.com/easternshorebrewing
Delight for four relaxing days in the food, history, and culture of Maryland's Chesapeake bay! You will ride along the historic Eastern Shore with the perfect mix of easy riding […]
Join us on the Talbot County Courthouse Lawn on April 25th, 2024 at 5PM as we celebrate the birthday of Talbot County. This special birthday celebration will include music from […]
Free Community Event. Food Trucks, Live Music, Emergency Equipment, Non-Profit Booths, Vendor Fair, and more! Venue: Centreville Middle School Event by Thomas Hayman and Centreville Middle School
VIP WineFest 2024 We are pleased to announce WineFest 2024! We are bringing back WineFest 2024. Wine will be tasted from many countries around the world! Wine will be poured, memories will be made and you may just leave with a new favorite! This VIP event will be held at the Old Brick Inn in […]
Blue Ruin is teaming up with One Mission Cambridge to host the Cambridge Craft Market and Food Drive! From 3pm to 9pm on Friday, April 26th, visit Blue Ruin’s parking lot and show room at 400 Race St to shop from over twenty vendors. There will be something for the whole family, from sweets to […]
Hidalgo is an epic biographical film based on the legend of the American distance rider Frank Hopkins and his mustang Hidalgo racing in 19th century Arabia against Bedouins riding pure-blooded […]
Uniquely arrive in charming St. Michaels, Maryland by boat! Depart from @kentmorrmarina and enjoy light appetizers with beautiful views to St. Michaels harbor, enjoy the Wine tasting crawl and re […]
Mark your calendar and plan to join us for Oxford Day, April 27, 2024. One of our most treasured events will begin at 8:30 – the Blessing of the Pets, […]
