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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4 events,
Hosted by: Classic Motor Museum St Michaels Where: 102 E. Marengo Street, St. Michaels Maryland. When: Every Saturday Morning 9 am to 11 am. From now through the end of March we have a "Coffee in the Barn" event every Saturday. This happens directly in the museum barn. It is free for members and $5 for non-members. It […] 
Join us every Saturday and Sunday at The Fool's Lantern for brunch and our Build-Your-Own Bloody Mary/Maria Bar! Choose from a variety of vodka or tequila, add our house made mix, and then choose from over 20 toppings to create your unique drink. Pair it with items from our brunch menu to start your weekends […] 
top by Simpatico's Courtyard or in the Shop at 104-106 Railroad Ave, just off Talbot Street, every weekend for free tastings of our hand-picked Italian wines! Peruse the shop and chat with our enthusiastic staff - We Love All Things Italian! We also offer free tastings all week long. Salute!
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Come and join Corah's Corner for our Annual Easter Brunch! We will have a Special Easter Brunch menu, a special kiddo menu, Bottomless Mimosas & Bloody Mary’s, Fun Craft Cocktail and More!!! LIVE Music with Sam Pugh starting at 11am!!! Reservations Preferred 410-745-8008 Venue: 105 N Talbot Street, Saint Michaels, MD Event by Corah's Corner |
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6 events,
Save the date! The Avalon Foundation’s Annual Multicultural Festival returns to Easton’s Idlewild Park with a fun day of diverse musical traditions, arts, and food on Saturday, May 4, 2024, from 10 a.m. to 2 p.m. A springtime favorite for 24 years on the Mid-Shore, the event celebrates the various cultures contributing to the rich […] 
Spring is in the air, and brighter days are ahead. Looking for a fun excuse to get out of the house? Well, look no further. Far Eastern Shore Winery will host a Spring Sip & Paint session on Saturday, April 27th. Tickets: $40 Event by Far Eastern Shore Winery Venue: 8370 Ocean Gateway, Easton, MD, United […]
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Corah's Corner will have Easter Brunch on Sunday, April 9th from 10am-3:30 pm- The Easter Bunny Brunch portion for the kiddos will be from 10-12 am! Parents! Here’s your photo opportunity!!!! It’s going to be our BEST, most delicious Easter Brunch yet!!!! Reserve spot: 410-745-8008 Venue: 105 N Talbot Street, Saint Michaels, MD |
6 events,
3 Weekends to browse, tour and shop new and used boats. The docks are connected from Safe Harbor Narrows South to Fisherman's Village with access to docks at Crab Deck and the Hyatt Place Kent Island. No cost to enter and no cost to park. Crab Deck is open during the event with […] |
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Come Hungry...Leave Happy! Taste Of St. Michaels includes a tasting crawl on Saturday, April 15th from 11 am - 4 pm. The Tasting Crawl allows participants to taste their way around St. Michaels at award winning restaurants and other participating businesses in town, including lodging and shops around the Town of St. Michaels. Each tasting venue will […] |
7 events,
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Celebrate the 20th anniversary of Chesapeake Bay Week with a special film festival, presented by CBMM in collaboration with Maryland Public Television. Dive deep into the Bay's rich history through the inspiring stories of the people who call it home. Throughout this three-day preview event, enjoy advanced screenings alongside panel discussions and expert talks, as […] |
7 events,
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Vintage Family Farms and Corah's Corner are teaming up again to bring you a create your own Tulip bouquet bar with our own field grown Tulips and your favorite Tequila Cocktails. Hosted at Corah's Corner outside deck, you will be able to relax with a cocktail while arranging flowers following your own inspiration in […] |
7 events,
The Eastern Shore Sea Glass and Coastal Arts Festival brings artisans and craftspeople who will exhibit and sell coastal and sea-glass related jewelry, home décor, art, and more. The popular festival runs 10am–5pm Saturday and 10am–4pm Sunday, with all tickets valid for admission on both days. Each ticket includes entrance to the Eastern Shore Sea […] |
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7 events,
VIP WineFest 2024 We are pleased to announce WineFest 2024! We are bringing back WineFest 2024. Wine will be tasted from many countries around the world! Wine will be poured, memories will be made and you may just leave with a new favorite! This VIP event will be held at the Old Brick Inn in […] |
7 events,
Uniquely arrive in charming St. Michaels, Maryland by boat! Depart from @kentmorrmarina and enjoy light appetizers with beautiful views to St. Michaels harbor, enjoy the Wine tasting crawl and re board to return to @kentmorrmarina. For more informarion about the Wine Crawl, please see the attached link. https://facebook.com/events/s/taste-of-st-michaels-april-27t/3530296007225037/ Event by Migrator Fishing and Hunting LLC […] |
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3 events,
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Sip cocktails and enjoy the sounds of JG and the Initials aboard PATRIOT while floating on the gentle waters of the Miles River on a 90-minute cruise. In the early 1990s, jazz cruises were a PATRIOT tradition, and we are excited to bring it back. Space is limited for this event. It will sell out […] |
3 events,
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Join us on Saturday, May 4th for JCT 33 on the patio! 6-9pm Live & Local! Let’s kick off our Music Season the proper way! Come JOIN us for some Great tunes Great food and Great Cocktails! Event by Corah's Corner Venu: Corah's Corner |
