Events on Maryland’s Eastern Shore

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.

All Day

Wine Tasting at St. Michaels Winery

Wine tastings Hours Monday - Saturday (12pm-5pm) Sunday (12pm-4pm)  With 18 wines in our cellar, we have something for every pallet. Tasting Fee: $1.00 per wine sampled Glasses:  Glasses of […]

$1
Ongoing

St. Michaels Farmer’s Market

The St. Michaels Farmers Market features farmers and vendors selling locally grown and caught vegetables, meats, and fish, plus handmade crafts and live music.The St. Michaels Farmers Market features farmers […]

Free

St. Michaels Yacht Beer Tasting Cruise

Available per person or Private Charter Join us for an unforgettable experience on our ice-cold Beer Tasting Cruises Be prepared for an unforgettable adventure on our beloved historic yacht Sail Selina II. Indulge in the aroma, taste, and quench your thirst with our cold, refreshing beers. A 2-hour tour on our beautifully kept sailing boat […]

$115

St. Michaels Yacht Wine Tasting Cruise

Enjoy a truly unforgettable wine tasting experience on the Chesapeake Bay with Sail Selina II. Our 2-hour St Michaels, MD wine tasting cruises are the perfect way to indulge in the basics of wine tasting while taking in breathtaking views of one of the most picturesque waterfronts in America. With limited availability for just six […]

$115

Easton Farmers Market

From local produce growers to watermen, from bakers to crafters and local artisans, the Easton Farmers Market provides an entire meal, home décor and unique gift items in a friendly and festive environment. The market is open every Saturday from April 15 to December 16, 2023 at 8 a.m. to 1 p.m. Live music starts […]

Free

St. Michaels Ghost Walk – Spirits of Rowdy Women

The walk begins in front of the Chesapeake Bay Maritime Museum and makes its way through around the St. Michaels harbor and around St. Michaels historic downtown. Visit an old […]

$25

Easton Music Bingo at Doc’s Downtown Grille

MUSIC BINGO - Free to play, Prizes to win! No ticket required, first-come, first-served. Possession of a ticket does not guarantee a seat at the gameshow. Contact the venue to discuss best time to arrive to get a seat. Play That Funky Bingo is like regular bingo but instead of calling numbers, we play parts of songs. […]

Feasting Over Fire Series with Chesapeake Chefs

Chestertown’s Brampton Inn and Chesapeake Chef Service are teaming up to present a series of alfresco dinner party’s highlighting the Eastern Shore’s farmers, watermen, cheesemakers, and many more. Reserve Your […]

Mid-Atlantic Small Craft Festival

Hundreds of amateur and professional boat builders, model boat builders and enthusiasts come from all over the region to display their skiffs, kayaks and canoes. Watch many of these one-of-a-kind […]

Free