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.
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8 events,
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 wine are available each and every day. We also will have sangria or mulled wine occasionally, depending on the weather and our whims. Bottles: After […]
$1
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 and vendors selling locally grown and caught vegetables, meats, and fish, plus handmade crafts and live music.
Free
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
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
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
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 cemetery and hear stories about St. Mary’s Square where ghosts of unremembered dead once haunted a school that was on the Square. Visit the Victoriana […]
$25
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. […] 
About the Sea Witch® Festival The annual Sea Witch Festival is Rehoboth Beach’s free family-friendly Halloween celebration. Dress up and enjoy the parades, live entertainment, contests and more in downtown Rehoboth Beach. The Sea Witch Festival is Friday through Sunday, Oct. 27-29, 2023. Sea Witch Festival Activities All through downtown Rehoboth, and at local businesses, […] |
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4 events,
More than 1,000 volunteers work year-round to stage the show, most coming back to lend their talents and time year after year. Art collectors find exceptional wildlife art from renowned master artists, along with a variety of events and vendors for all to enjoy that display everything from fishing lures to all-terrain vehicles and boats. […] |
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3 events,
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Join us as we begin the holiday season featuring beautifully carved Ice Sculptures sponsored by the Berlin businesses! 30+ Holiday themed lighted sculptures Tree is lit at 6pm Greet Santa at Kringle Kottage at the Taylor House Museum Music by DJ Big Al Reno – Shops open late! |
3 events,
“Caroling, Caroling Through the Town” is the theme for the 2023 Festival of Trees which will be held in The Gold Room of The Tidewater Inn from Saturday, November 25 to Tuesday, November 28, 2023. In a magical holiday setting, fifty beautifully decorated trees sponsored by individuals and businesses will be on display. In addition, […] |
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