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 […]
$3
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
Wine & Unwind with Marianna Styles Sunday, July 9, 2023 from 1:00 PM to 4:00 PM EDT Sip wine, enjoy live music by Marianna Styles No fee, no reservation. Layton's Chance Vineyard & Winery Summer Concert with Uprizing Saturday, July 22, 2023 from 6:00 PM to 9:00 PM EDT Uprizing will be playing music […]
Free
Offers small plates with intense flavors and specializes in over 150 different kinds of cocktails! Join Blue Ruin for live music on these dates! July 14th - Bryan Russo 8-10pm July 21st - Jayme Dingler 8-10pm July 22nd - Garrett Roe Karaoke 7-10pm July 28th - Alli Pinsky 8-10pm July 29th - Sam Pugh 7-10pm […]
Free
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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 music, community non-profit groups serving great homemade food from pit beef to peach cobbler, local vendors offering their best hand-made crafts, and lots of great […]
Free
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Held rain or shine since 1946, the Annual Rotary Crab Feast is one of the longest-running and most popular summertime traditions in Annapolis! Known as “the world’s largest crab feast,” the all-you-can-eat (and drink) event invites folks from near and far to get their fill of Maryland’s famous blue crabs – plus Maryland vegetable crab soup, sweet […]
$90
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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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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 of the summer in Easton with the soulful and swinging sounds of Jazz. This premier event will captivate music lovers and jazz enthusiasts alike and […] |
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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 […]
$85
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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 […] |
