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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Operating May through November in 2023, 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 River […]
Free
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1 event,
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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
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3 events,
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
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5 events,
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
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Come out to the Jetty Restaurant and Dock bar for amazing food and the best drinks in the area! Enjoy the beautiful view and if you are feeling the vibes come rock the dock with Karaoke night. Every Wednesday from 6:30 – 9:30 head to the Jetty restaurant and Dock Bar for Karaoke night.
Free
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5 events,
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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
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7 events,
The oldest active powerboat race in the country happens right here in Dorchester County, Maryland. This year's race will be held on May 20-21, 2023 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 a day charge […]
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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
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On Saturday and Sunday, the prestigious juried exhibit draws a wide selection of regional collectors as well as from major cities along the Eastern Seaboard. The much-anticipated annual show is well known throughout the area and celebrated as the season’s “kick-off” for art lovers. The exhibit featuring 36 artists from the mid-atlantic region and beyondis […]
$5
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5 events,
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Come out to the Jetty Restaurant and Dock bar for amazing food and the best drinks in the area! Enjoy the beautiful view and if you are feeling the vibes come rock the dock with Karaoke night. Every Wednesday from 6:30 – 9:30 head to the Jetty restaurant and Dock Bar for Karaoke night.
Free
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7 events,
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
The CMM is proud to bring our community together in honoring the service of our military heroes by hosting the Annual Classic Motor Museum Parade. The participants will line up at Perry Cabin Park, and will head down Talbot St, pausing near Railroad Avenue for the emcee to announce the make, model, and driver of […]
Free
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Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew. Advance reservations are recommended and accepted online use the link below, until midnight of the day before the sail. We carry up to 20 passengers per […]
$40
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7 events,
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
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11 events,
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
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Come sail away with Kalmar Nyckel for a 2.5-hour sail and have an adventure of a lifetime! The Tall Ship of Delaware returns to Cambridge, MD on Friday, June 2 through Sunday, June 4. Discover the remarkable story behind Kalmar Nyckel, a full-scale replica of the merchant ship that brought Swedish settlers to North America […]
$65
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Looking to go sailing at sunset while sipping champagne? This is the sunset champagne charter for you! Come join us for a relaxing 2 hour cruise near Annapolis. Your St Michaels MD sail boat ride includes a personalized tour with our first class captains & crew on all our boating trips including our romantic sunset […]
$115
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15 events,
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
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Come sail away with Kalmar Nyckel for a 2.5-hour sail and have an adventure of a lifetime! The Tall Ship of Delaware returns to Cambridge, MD on Friday, June 2 through Sunday, June 4. Discover the remarkable story behind Kalmar Nyckel, a full-scale replica of the merchant ship that brought Swedish settlers to North America […]
$65
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On June 3rd, from 12:00 pm - 4:00 pm come out to the St. Michaels Brewfest 2023! They offer Three Pouring Venues, Over A Dozen Breweries, Art, Glassware, Food, and more! Tickets are limited and can be purchased on the website below, Offering General admission and a VIP cruise tickets are still available! St. Michael's […]
$55 – $110
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With over 6,000 people in attendance, 2019 launched the Inaugural Annapolis Pride Parade & Festival– a visual dreamscape of the human spirit at its best. People, children, and pets of every walk of life dress in their rainbow finest and line the sidewalks of West Street to witness a dazzling parade of floats, dancing spirit dragons, […]
Free
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