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.
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6 events,
VALENTINE'S DAY 2024 NOW OPEN FOR BOOKINGNew this year: We are partnering with Tiger Lily for the ultimate Valentine's experience! Have a romantic carriage ride around Easton followed by dinner ON US at Tiger Lily! Riding and Driving lessons can be booked by clicking BOOK NOW. Please email [email protected] or text 540-460-2455 for private rentals and driving lessons. […] 
About this event Far Eastern Shore Winery invites you to join us for our Sip & Stitch Sundays series. We’ve had so much fun the past two Sip & Stitch Events over Halloween weekend and, more recently, on Small Biz Saturday, we thought we’d try to grow our stitching network. We’ll be hosting informal crochet […] 
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 |
6 events,
The 8th annual Eastern Shore Sea Glass and Coastal Arts Festival in St. Michaels, Md. will now have a larger, waterfront location at the Chesapeake Bay Maritime Museum (CBMM). The Sea Glass Festival will be at CBMM on Saturday, April 6 from 10–5 pm. and Sunday, April 7 from 10-4 pm. The new venue also expands […]
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Attention beer enthusiasts! HOPS into Spring at the Kent Narrows Brew Fest! This is a 21+ event. General Admission tickets are $50. Designated Driver tickets are $20. Tickets: https://kentnarrowsbrewfest.ticketleap.com/?fbclid=IwAR3mydSgN8kVIOX2dMtbJWqNVnjip3NLK5Y4faFWxIwv8osGMKHqM_f9qec Come support local craftsmanship and perhaps discover a new favorite! Craft beers are created with passion and creativity, resulting in a wide array of flavors and […] |
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7 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 |
8 events,
Join us for the first outdoor pig roast and open pit chicken BBQ of the season! Pulled Pork Sandwiches and all the fixings, plus that delicious fresh bbq chicken! Don't miss it! Event by Amish Country Farmers Market in Easton, MD Amish Country Farmers Market in Easton, MD 
Immerse yourself in the enchanting flavors and cultural richness of Greece at our monthly Greek food experience! Discover an enticing assortment of cheeses, ranging from creamy feta and Manouri, to aged Graviera and Kefalotyri, complemented by an exquisite selection of Mediterranean olives, traditional Greek spreads. Sip and savor the complexity of Greek wines, each bottle […] |
10 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 […] 
8:30pm - 12:30a no ticket, just pay the cover Event by The Reagan Years - The East Coast’s Original 80s Tribute Band Venue: Jetty Dock Bar |
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9 events,
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Sunday April 14 4-6pm Tickets: $46 Join us for a fun creative evening at Alibi Gastropub in Centreville to create our newest piece. We will be using paint and tumbled sea glass to create our coastal inspired blue crab. Seasoned crafters and beginners welcome. Don’t forget it’s happy hour all day long so come out […] |
9 events,
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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 […] |
9 events,
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Paint Night: Unleash your inner artist Make a masterpiece out of your night out! Grab your friends and join us this week for an Original Paint Nite party. Our talented local artist Kristi Egner will guide you through all the steps to create your chosen painting in under two hours. You won't believe what you […] |
9 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 […] |
9 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 […] |
10 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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Event by Big Mack’s Kitchen Venue Eastern Shore Brewing https://www.facebook.com/easternshorebrewing |
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9 events, |
9 events,
Delight for four relaxing days in the food, history, and culture of Maryland's Chesapeake bay! You will ride along the historic Eastern Shore with the perfect mix of easy riding , gorgeous scenery, sumptuous seafood, boutique shops, and classic bayside towns from the 1600s. Explore at your own pace with our SAG wagon always nearby […] |
9 events, |
11 events,
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Join us on the Talbot County Courthouse Lawn on April 25th, 2024 at 5PM as we celebrate the birthday of Talbot County. This special birthday celebration will include music from local community groups, a keynote speaker, and of course, birthday cake! During the ceremony, we will also highlight the nominees for the Talbot Citizen and […]
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Free Community Event. Food Trucks, Live Music, Emergency Equipment, Non-Profit Booths, Vendor Fair, and more! Venue: Centreville Middle School Event by Thomas Hayman and Centreville Middle School |
12 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 […]
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Blue Ruin is teaming up with One Mission Cambridge to host the Cambridge Craft Market and Food Drive! From 3pm to 9pm on Friday, April 26th, visit Blue Ruin’s parking lot and show room at 400 Race St to shop from over twenty vendors. There will be something for the whole family, from sweets to […]
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Hidalgo is an epic biographical film based on the legend of the American distance rider Frank Hopkins and his mustang Hidalgo racing in 19th century Arabia against Bedouins riding pure-blooded Arabian horses. Starring Viggo Mortensen and Omar Sharif. Relax at a table for two with drinks and slices from Roma Event by The Ebenezer Theater […] |
11 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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Mark your calendar and plan to join us for Oxford Day, April 27, 2024. One of our most treasured events will begin at 8:30 – the Blessing of the Pets, followed by the Talbot Humane Dog Walk which finishes at Town Park for the annual Dog Show. Parade Route A Family Hour of fun games […]
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Mosaic Mushrooms! Saturday, April 27th 10am-2pm 10 South Hanson St, Easton, Md $125 Mosaic a 3-D mushroom sculpture using stained glass, ceramics, mirror, beads and agates found in my 5 room studio in Easton! No Experience necessary! Mushrooms stand 18” tall and are created out of durable outdoor materials. Perfect for a fun spot inside […] |
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8 events,
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Come join us at the farm for the unicorn festival. Take a picture with Dominic’s very own unicorn, visit with the farm animals, take a barrel ride and enjoy the play area, come dressed in your favorite unicorn outfit. Pre registration preferred. $10 a child Message Kelly for more information 443-496-1710 Event by Kelly […] |
5 events,
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• Bring in any indoor/outdoor plants, seeds, plant/garden books, tools and take something fun and new home! • Please make sure that all items are clean and pest free. • Label all plants with names and as much important information as possible. • All plants should be in soil or rooted in water. Lunch is […] |
4 events,
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Join Megan from Sprinkle It Sweet at Ten Eyck Brewing Company in Queenstown, Maryland. In this 2 hour class, you'll learn how to decorate five pre-baked cookies with royal icing and pre-made sugar embellishments! No experience is necessary, everything you'll need is provided at class including boxes to transport your yummy creations home to enjoy! […] |
5 events,
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Join us in downtown Easton, MD for a spring celebration! Easton will be decked out in flowers, bows, and bouquets for a lovely spring celebration. Merchants will be competing for the "Best Dressed." Dazzling floral arrangements, an outdoor movie night, horse carriage rides, retail specials, free & ticketed live music, and more! Full details can […]
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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 […] |
5 events,
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Food, Corn-hole, and much more start at 3 the fabulous Kick Back Band will start playing around 6 Tickets are available for Purchase at the VFW 410-827-8194 Venue: Grasonville Memorial Vfw Event: Event by Dana Keller and Kent Island Happenings
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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 |
