Events on Maryland’s Eastern Shore

 
Looking for something to do in Maryland’s Eastern Shore? You’re in luck! The area is full of exciting events that are sure to delight locals and visitors alike. Whether you’re interested in food and drink festivals, live music, art exhibits, or cultural celebrations, there’s always something happening in this vibrant community.
 

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 5k (3.1 miles) run, all from the grounds of Great Marsh Park, located at 0 Somerset Avenue, Cambridge. THE HALF MARATHON COURSE IS NORMALLY AN […]

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 will make her feel truly appreciated, and every mom will receive a complimentary glass of champagne to add a touch of sparkle to her special […]

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 on Sunday, May 12th. Enjoy a rousing afternoon of wine or slushies, unforgettable memories with Mom, and, of course, painting! Get $5 Off with promo […]

2024 Cambridge Classic Powerboat Regatta

Racing since 1911, the oldest active powerboat race in the country happens right here in Dorchester County, Maryland. This year's race will be held on May 18-19, 2024 on the Choptank River. About 70 boats are expected to be on hand to create an exciting two days of racing. Admission is FREE with a $5 […]

43rd Annual Strawberry Festival in Ridgely

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

Chamber Music Festival 2024

Ebenezer Theater 17 S Washington St, Easton, MD, United States

More information coming soon!

St. Michaels Brew Festival

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 […]

IRONMAN 70.3 Eagleman

Gerry Boyle Parl Somerset Ave, Cambridge, MD, United States

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 […]

36th Annual Antique and Classic Boat Festival and Costal Arts Fair in St. Michaels

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 […]

Adult Field Day at the Layton’s Chance Winery in Cambridge

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 competition. Get ready to unleash your inner child with a series of classic field day games, all with an adult-friendly spin. Wear your favorite retro […]

The Famous Annapolis City fireworks from the Water

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 seats to the see fireworks! Memories are sure to be made. Book Today: www.TourBoatAnnapolis.com (443)333-1030 Event by Tour Boat Annapolis Venue: Annapolis, MD

Wine & Design Wine Bottle Bird Feeder at Layton’s Chance in Cambridge

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 be ready to hang when you leave. *DIY construction kits are also available Tickets: https://lp.constantcontactpages.com/ev/reg/deyws5z?fbclid=IwZXh0bgNhZW0CMTAAAR1Jc37b03FOtZR_qjtG5K6brKHF6Ai7L4nDIEgq-Q2f6VyUNlV63xFbem0_aem_AdmWSRPOrHfzIy0ylJzcCx47Zfi6RhR8gBOs9pZwVT3c_KUdAuOJBXeL09393JKgHluvhtdyEv88FC3az22YkRdV Organizer: Event by Layton's Chance Vineyard & Winery Venue: Layton's […]