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.
Friday, August 4 6PM until Fireworks Saturday, August 5 10AM – 4PM Sudlersville Peach Festival is co-hosted by the Sudlersville Volunteer Fire Company. With the best local bands providing live […]
Make your plans now for Labor Day Weekend and the Jazz Experience at The Avalon Theatre! The Avalon Theatre invites you and your friends to enjoy the unofficial end […]
Take a relaxing 3-hour cruise and live show on one of the most exciting attractions offered on Maryland’s Eastern Shore! The boat offers a fully enclosed lower deck with heating […]
Hunters Tavern will be doing a special $5 first Friday all summer long starting June 3rd! With $5 drafts, $5 glasses of house wine, $5 flatbread, and more, your Fridays […]
Make your plans now for Labor Day Weekend and the Jazz Experience at The Avalon Theatre! Date September 1, 2023 8:00 pm - 10:00 pm Sammy Miller and the Congregation: […]
Make your plans now for Labor Day Weekend and the Jazz Experience at The Avalon Theatre! SUN 9/3 3:00pm-6:00pm AVALON JAZZ EXPERIENCE ALLAN HARRIS: KATE’S KITCHEN The Avalon Theatre […]
The annual LIGHT NIGHT is Saturday, September 9, 2023, at the Cambridge Yacht Club. A celebration of the Choptank River Lighthouse and the difference “The Jewel of the Choptank” is […]
At IRONMAN Maryland, part of the VinFast IRONMAN North America Series, race day does not make us individuals that are competing against ourselves. When we toe the line, we become a team of […]
Carroll County’s 39th Maryland Wine Celebration! An Outdoor Event Featuring Wine, Live Music, and Local Vendors. Explorer Pass | $65* Enjoy an upgraded Maryland Wine Festival experience. The Explorer Pass includes admission to the Main Field, the Maryland Wine Explorer Village and includes: • Exclusive, curated Maryland-grown wine samples • Admission to an exclusive seating […]
It's that time of year!!! Zeta Phi Beta Sorority, Incorporated, Iota Chi Zeta Chapter will host it's annual "Wine Down". This fun for all event will be held on Saturday, […]
Take a relaxing 3-hour cruise and live show on one of the most exciting attractions offered on Maryland’s Eastern Shore! The boat offers a fully enclosed lower deck with heating […]
Crab Feast 2023 is finally here! Join us on Sun Sep 17, 2023 at 2 Pythian Drive Edgewater, MD 21037 for a day of fun, food, and festivities. This in-person event is perfect for all crab lovers out there. Get ready to indulge in the freshest and most delicious crabs you've ever tasted! Our event will start at 2:00 PM Eastern […]
