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.
Music, food, Strawberry Shortcake, Entertainment, Children's activities, Parade, Craft vendors, Strawberry Chase, Informational booths, Model Train Display and so much more! Event by Brenda Walls Martin Sutton Memorial Park 232 W 4th St, Ridgely, MD 21660, United States
More information coming soon!
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 Summer Hefeweizens and Pilsners to IPA's and Complex Porters. The historic harbor of St. Michaels, Maryland, attendees can casually stroll between three different pouring venues […]
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 while enjoying the vibrant art scene, local restaurants and breweries, fresh seafood, and family-friendly adventures. With over 25 years of racing, get ready to soar towards the finish […]
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 Fishing”. Come see amazing antique boats, classy classic boats, and awesome vendors! Registration for vendors and boats is open now! Venue: Chesapeake Bay Maritime Museum […]
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 […]
Each guest will sand and stain or paint their own bird feeder. Choose your recycled Layton's Chance wine bottle and fill with bird seed before you go! Your feeder will […]
Come join us for a fun-filled day celebrating Frederick Douglass with crabs, cars, and bikes! Welcome to the Inaugural Frederick Douglass Unit Day Crab Feast Car and Bike Show! Join […]
We are so excited to welcome Giuliano Hazan, Italian cookbook author and educator, to Trattoria Simpatico for 2 very special cooking classes and Wine Dinners, the first is Saturday, June […]
TICKETS AVAILABLE AT: https://hiphoprnbyachtpartyJune30.eventbrite.com Why party in the club when you can party on a yacht!!! Join us as we cruise out of Annapolis for The Hip Hop R&B Yacht […]
The Wailers are a rare breed of musicians who have earned their place in the annals of music history. Their culture-defining music, embodying the spirit of the ‘70s reggae movement, […]
