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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3 events,
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 […] 
Event by Prodigal Creations Of Princess Anne Venue: 1000 goodwill ave Cambridge Md Tickets: https://l.facebook.com/l.php?u=https%3A%2F%2Fsquare.link%2Fu%2FfErOwYqZ%3Ffbclid%3DIwZXh0bgNhZW0CMTAAAR0KbCjOiy2Aa42_hIhL3dOfi4Ph4WHnAT8hWN2BpgDUHAyVbeinGzFyLxA_aem_AdUE1ZDJadUPgWXmDf4nZ8-3qPkAa3jAx5yj79L_4jq5VB9meuy0eCDjqzdxWb_Jv888iL_eklZln32zm3Qi4Wqq&h=AT0rSgshAHtpyMe4RIfBDkY0VNO8Cmu7sUSTXQdUSY-XFPtnEOLWDsopCCjSiCy7I3CPcWaSELMhkj0OzUySVKM0XZX2Zx9oGQu_ZesJC6F7SkF2IjjNra_AHD8OjuQ15gALFEC8OfsTNzf78FSvkQiWMWE
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Music, food, Strawberry Shortcake, Entertainment, Children's activities, Parade, Craft vendors, Strawberry Chase, Informational booths, Model Train Display and so much more! Event by Brenda Walls Martin Sutton Memorial Park 232 W 4th St, Ridgely, MD 21660, United States |
3 events,
The St. Michaels Community Center is pleased to announce our 2024 schedule for our Concerts in the Park series, kicking off on Thursday, May 30, 2024 and continuing every Thursday through August 29 (except July 4) beginning at 6 p.m. at the waterfront Muskrat Park in St. Michaels. Concerts feature fabulous local talent on the […] |
3 events,
Venue: West St, Annapolis, MD 21401, United States Event by SoulJourners Only for June 1st starts at 6pm Stay up to date this is first of several DUTS shows with Souljourners for 2024! |
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6 events,
Kent Island Yacht Club will host two prestigious events this year – the 8th annual Chesapeake Bay Motoring Festival on June 8-9, and the 17th annual St. Michaels Concours d’Elegance on Chesapeake Bay on September 27-29. Both events are presented by St. Michaels Concours d’Elegance on Chesapeake Bay. Venue: Kent Island Yacht Club The event […]
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St. Michaels Brewfest is celebrating 10 years! Brewfest continues to bring specially crafted regional and National beers to this Pre Summertime Beer Festival! Offering the full spectrum of beers from Summer Hefeweizens and Pilsners to IPA's and Complex Porters. The historic harbor of St. Michaels, Maryland, attendees can casually stroll between three different pouring venues […] |
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6 events,
Take Flight and Soar An authentic Chesapeake town on Maryland’s storied Eastern Shore, lies the historic IRONMAN 70.3 Eagleman. A big race for a small town, experience Cambridge’s history and charm while enjoying the vibrant art scene, local restaurants and breweries, fresh seafood, and family-friendly adventures. With over 25 years of racing, get ready to soar towards the finish […] |
6 events,
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6 events,
Sip | Savor | Shop invites you to join us for an evening of culinary delights and shared moments. At the event, you can sample our Greek gourmet products, including a red and white wine, artisanal hard and soft cheeses, filo-wrapped delights like spanakopita and tiropita, a variety of Greek olives, and some of the […] |
7 events,
We cannot wait for the 36th Annual Antique and Classic Boat show at the Chesapeake Maritime Museum in beautiful Saint Michael’s, Maryland. This year, the theme is “It’s All About Fishing”. Come see amazing antique boats, classy classic boats, and awesome vendors! Registration for vendors and boats is open now! Venue: Chesapeake Bay Maritime Museum […] |
9 events,
The Easton Maryland Farmers Market has been operating for over 40 years. Located in the municipal parking lot in the 100 block of North Harrison Street the pedestrian-only market features live music every Saturday at 10:30. All of our vendors are cultivating, producing, cooking and crafting their inventories so be sure to stop by and […] 
Dance the night away with music by Classic Vibe. FREE to attend. Food and fun! Cash Bar with all proceeds going to Downtown Snow Hill, Inc. Venue: Event by Downtown Snow Hill in Sturgis Park Organizer: Sturgis Park |
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8 events,
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7 events,
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8 events,
Let's Do Trivia! is a weekly, team-based, live-hosted pub and restaurant trivia game show. FRIENDS * FOOD * FUN! FREE TO PLAY - BIG PRIZES TO WIN! $40 First Place + more! Our team-based trivia game is perfect for groups of friends, family, or co-workers. Let's Do Trivia! gives you time to answer questions while […] |
8 events,
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8 events,
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8 events,
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9 events,
Get ready for the ultimate seafood extravaganza of the summer! This event has premium crabs measuring 6 1/4" up to 8"! 97.5FM DJ, Big Mark will be mixing up the R&B/Hip Hop hits from 90's and 00's on the upper level of the cruise while music plays on the lower level. Hurricane Hazel will be […] |
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10 events,
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Step back into the carefree days of childhood with a twist at our Adult Field Day at the Winery. This event promises a delightful blend of nostalgia, fun, and friendly competition. Get ready to unleash your inner child with a series of classic field day games, all with an adult-friendly spin. Wear your favorite retro […] |
9 events,
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9 events,
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12 events,
Event by Foxy's Harbor Grille Venue: 125 Mulberry St, Saint Michaels, MD, United States, Maryland 21663 TODAY Groove Tide 5-8pm FRIDAY Uncle Ward 5-8pm SATURDAY Mike Miller 4-7pm SUNDAY Brandon & Thordis 4-7pm Be sure to check out our Events Tab on Foxy’s Facebook to see our Live Music Schedule for the summer! 🎶☀️ https://www.facebook.com/FoxysHarborGrille/events 
Family Fun Carnival! On July 4th the Carnival will be open from 4-11pm and as soon as it gets dark the fireworks will light up the sky! Wristbands offered nightly!!! Excluding the 4th Event by Shaw and Sons Amusements Venue:Grounds behind Target, 28539 Marlboro Avenue, Easton.
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Come celebrate your Independence with us. Enjoy the famous Annapolis City fireworks from the water! Public 3 hour cruise includes a tour around the harbor, sunset, and then front row seats to the see fireworks! Memories are sure to be made. Book Today: www.TourBoatAnnapolis.com (443)333-1030 Event by Tour Boat Annapolis Venue: Annapolis, MD |
12 events,
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Each guest will sand and stain or paint their own bird feeder. Choose your recycled Layton's Chance wine bottle and fill with bird seed before you go! Your feeder will be ready to hang when you leave. *DIY construction kits are also available Tickets: https://lp.constantcontactpages.com/ev/reg/deyws5z?fbclid=IwZXh0bgNhZW0CMTAAAR1Jc37b03FOtZR_qjtG5K6brKHF6Ai7L4nDIEgq-Q2f6VyUNlV63xFbem0_aem_AdmWSRPOrHfzIy0ylJzcCx47Zfi6RhR8gBOs9pZwVT3c_KUdAuOJBXeL09393JKgHluvhtdyEv88FC3az22YkRdV Organizer: Event by Layton's Chance Vineyard & Winery Venue: Layton's […] |
11 events,
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13 events,
We are so excited to welcome Giuliano Hazan, Italian cookbook author and educator, to Trattoria Simpatico for 2 very special cooking classes and Wine Dinners, the first is Saturday, June 29th, 5 to 8 PM and the second is Sunday Pranzo, June 30th, 12:30PM to 3:30 PM. Giuliano teaches his special courses in Sarasota, FL, […]
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Come join us for a fun-filled day celebrating Frederick Douglass with crabs, cars, and bikes! Welcome to the Inaugural Frederick Douglass Unit Day Crab Feast Car and Bike Show! Join us at the Veterans of Foreign Wars for a day filled with delicious crab, stunning cars, awesome bikes and double dutch competition! Get ready to […] |
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12 events,
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TICKETS AVAILABLE AT: https://hiphoprnbyachtpartyJune30.eventbrite.com Why party in the club when you can party on a yacht!!! Join us as we cruise out of Annapolis for The Hip Hop R&B Yacht Party!! WE OUTSIDE!!! THE HIP HOP R&B YACHT PARTY is the only party you want to be at on a Sunday!!! Get ready to dance […] |
10 events,
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10 events,
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11 events,
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The Wailers are a rare breed of musicians who have earned their place in the annals of music history. Their culture-defining music, embodying the spirit of the ‘70s reggae movement, has left an indelible mark on the industry. Experience the magic of their timeless classics and incredible cuts from Bob Marley’s vast repertoire in a […] |
15 events,
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Join our downtown retailers as they clear out their racks and make room for new inventory at the 4th of July Sidewalk Sale! This annual sale always offers BIG savings on clothing, apparel, home furnishings, and more. The participating stores: LaDeDa, Lizzy Dee, Marc Randall, The Mercantile, Vintage Books and Windswept Clothiers. You can’t find […]
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Come spend the 4th doing some day drinking with right on the beautiful Miles River!!
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Dance the night away under the sparkle and glitter that only fireworks can bring. The carnival opens every night at 6:00 pm until 10:00 pm. Wristbands are $30 per person giving unlimited access to all rides. Live music on the 4th of July starts at 6:00 pm with opening ceremonies at 7:00. The fireworks will […] |
11 events,
On First Friday the art galleries of downtown Easton extend their hours and invite you on a tour of artistic adventure – openings, lectures, book signings, and more! View new art exhibits, meet the artists, and discover sales and great deals. Enjoy dinner and drinks at one of our restaurants, stroll downtown, and spend the […]
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Jul 5: Town of Oxford Fireworks – 8:30 – 9:30 PM. Sponsored by the Tred Avon Yacht Club The Oxford fireworks show celebrates Independence Day on the “Strand” Venue: The beautiful riverside street along the Tred Avon River. Watch the sky light up with this beautiful fireworks display beginning at duck, usually around 9 PM. […] |
12 events,
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In celebration of Independence Day, the Chesapeake Bay Maritime Museum will host Big Band Night on July 6, inviting guests to bring lawn chairs and picnic blankets for an evening of music, dancing, and fireworks along the Miles River. The doors open at 6pm before the music begins at 7pm. The Shades of Blue Orchestra […]
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2024 Fireworks in St. Michaels Harbor! Scheduled for Saturday night July 6, 2024, shortly after dusk 8:30pm to 10-10:30pm With a rain date on July 7, 2024. Bring your lawn chairs and find a good spot in town! The Chesapeake Bay Maritime Museum will be open to the public for viewing. Or, come by boat […] |
