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.
Kent Island Yacht Club will host two prestigious events this year – the 8th annual Chesapeake Bay Motoring Festival on June 8-9, and the 17th annual St. Michaels Concours d’Elegance […]
St. Michaels Brewfest is celebrating 10 years! Brewfest continues to bring specially crafted regional and National beers to this Pre Summertime Beer Festival! Offering the full spectrum of beers from […]
Take Flight and Soar An authentic Chesapeake town on Maryland’s storied Eastern Shore, lies the historic IRONMAN 70.3 Eagleman. A big race for a small town, experience Cambridge’s history and charm […]
Sip | Savor | Shop invites you to join us for an evening of culinary delights and shared moments. At the event, you can sample our Greek gourmet products, including […]
We cannot wait for the 36th Annual Antique and Classic Boat show at the Chesapeake Maritime Museum in beautiful Saint Michael’s, Maryland. This year, the theme is “It’s All About […]
The Easton Maryland Farmers Market has been operating for over 40 years. Located in the municipal parking lot in the 100 block of North Harrison Street the pedestrian-only market features […]
Dance the night away with music by Classic Vibe. FREE to attend. Food and fun! Cash Bar with all proceeds going to Downtown Snow Hill, Inc. Venue: Event by Downtown […]
Let's Do Trivia! is a weekly, team-based, live-hosted pub and restaurant trivia game show. FRIENDS * FOOD * FUN! FREE TO PLAY - BIG PRIZES TO WIN! $40 First Place […]
Get ready for the ultimate seafood extravaganza of the summer! This event has premium crabs measuring 6 1/4" up to 8"! 97.5FM DJ, Big Mark will be mixing up the […]
Step back into the carefree days of childhood with a twist at our Adult Field Day at the Winery. This event promises a delightful blend of nostalgia, fun, and friendly […]
Come celebrate your Independence with us. Enjoy the famous Annapolis City fireworks from the water! Public 3 hour cruise includes a tour around the harbor, sunset, and then front row […]
Event by Foxy's Harbor Grille Venue: 125 Mulberry St, Saint Michaels, MD, United States, Maryland 21663 TODAY Groove Tide 5-8pm FRIDAY Uncle Ward 5-8pm SATURDAY Mike Miller 4-7pm SUNDAY Brandon […]
