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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The 4-mile long Wildlife Drive is open from sunrise to sunset every day, takes you through several types of wildlife-rich habitat found at Blackwater National Wildlife Refuge. Wildlife Drive is paved, and can be accessed by vehicle, bicycle, or foot. An entrance fee is required for the Drive, and can be paid at the […]
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The market with a U-Pick strawberry, blackberry, blueberry and cherry patch, U-Cut flower patch, and a beautiful selection of hanging baskets, perennials, annuals, and planters straight from their own greenhouse. Delicious homemade desserts are made daily. The market offers the freshest and sweetest homegrown sweet corn and tomatoes starting in late June as well as […]
Free
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
Once the oldest working courthouse in Maryland now currently the Old Courthouse Distilling was established in 2019! Distillery Hours Wednesday - 3:00pm to 9:00pm Thursday - 3:00pm to 9:00pm Friday - 3:00pm to 9:00pm Saturday - 2:00pm to 9:00pm Blanco Rum This rum is twice distilled, then cut and charcoaled filter for a super smooth […]
$10
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
Take a relaxing 3-hour cruise on one of the most exciting attractions offered on Maryland’s Eastern Shore! The boat offers a fully enclosed lower deck with heating and air conditioning, as well as a covered upper deck with a great view of the river. Catered by Suicide Bridge Restaurant and features local seafood and Eastern […]
$75
Operating May through November in 2023, Every Thursdays from 3pm – 6pm, the Long Wharf Farmer’s Market is a local favorite! What’s better than a waterfront Farmer’s Market? The market is situated in the Long Wharf park, nearby public parking. The market is within walking distance to the Municipal Marina, Skipjack Nathan, the replica Choptank […]
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
With over 30 local vendors at KENT ISLAND FARMERS’ MARKET at Cult Classic Brewery Year-round every Thursday. Hours 3:30- 6pm through Spring, Summer and Fall. January through March 3:30- 5:30. Experience local selection of seasonal fruits and vegetables. Hand crafted jewelry, crafts, home decor and more! Homemade baked goods, beauty products, local breweries and restaurants […]
Free
Only market in the heart of downtown Berlin featuring more than 30 farmers, bakers, food cultivators and more. Shops in the downtown also open early on Sundays. Live music starts at 10am. Free to attend, free to park! Farms: Bennett Orchards: Peaches and Blueberries (in season only) BayBees Farm: Honey Assateague Farm: Flowers Bratten […]
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
Enjoy outdoor dining and music on Wednesday and Saturday evenings 5pm-10pm May 20th-September 23rd on Inner West Street in Annapolis. The streets are filled with café tables, live music and dancing. Reservations are encouraged. |
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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 just got much better!
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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: The Music of 1973 The Avalon Theatre invites you and your friends to enjoy the unofficial end of the summer in Easton with the […] |
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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 invites you and your friends to enjoy the unofficial end of the summer in Easton with the soulful and swinging sounds of Jazz. This premier […] |
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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. […] |
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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 making for our community, the event will feature heavy appetizers, fun auctions, a “wine wall,” dancing, and much more. Outdoor tented space available in addition […] |
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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 Seat at the Table: Feasting Over Fire Dinner Series with Chesapeake Chef Service at Brampton Inn Experience a quintessential Eastern Shore tradition and join us […] |
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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 athletes that join forces to overcome whatever challenges race day brings. We are allies that stick by each other and offer words of encouragement. And […] 
Artisan Market featuring local artisans! We will have a DIY craft, flower bar, craft beer, food and music! No cost to attend! Rain or shine- we will set up outside weather permitting. This is two events in 2023! September 16: 11am-3pm December 2nd: 4pm-10pm
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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 […]
$65
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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, September 16, 2023 at Layton's Chance Vineyard from 4:30-8:00 pm. Tickets are $45 (until July 1st) which includes wine tasting, food, and entertainment. After July […]
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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 and air conditioning, as well as a covered upper deck with a great view of the river. Catered by Suicide Bridge Restaurant and features local […]
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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 […]
$90
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16 events,Make your plans now to join us in Salisbury, Maryland, for the Maryland Folk Festival— a diverse celebration of arts, culture, and heritage. This large-scale multi-day outdoor event, celebrates the roots, richness and variety of American culture. It features hundreds of the nation’s finest musicians, dancers, craftspeople and other keepers of culture in performances, workshops, […]
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Save the dates! The 2023 Chesapeake Film Festival (CFF) will be LIVE Sept. 30 and Oct. 1 at two historic venues in Easton, MD. The Festival goes VIRTUAL October 2 through 8, bringing you more fabulous films to watch anytime, anywhere. The hybrid festival begins with a LIVE weekend (Sept. 30 and Oct. 1) featuring […] |
