Events on Maryland’s Eastern Shore

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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  • 17th annual St. Michaels Concours d’Elegance on Chesapeake Bay & 8th Annual Chesapeake Bay Motoring Festival

    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 […]

  • St. Michaels Brew Festival

    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 […]

  • Sip | Savor | Shop in Easton

    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 […]

  • 36th Annual Antique and Classic Boat Festival and Costal Arts Fair in St. Michaels

    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 […]

  • Easton’s Farmers Market

    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 […]

  • Dancing Under the Stars in Snow Hill

    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

  • Easton Trivia Nights at Doc’s Downtown Grille

    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 […]

  • Old School R&B Crab & Cruise in Crisfield

    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 […]

  • Live Music all Summer at Foxy’s Harbor Grille in St. Michaels

    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

  • Easton’s 4th of July Celebration Carnival

    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.

  • Inaugural Frederick Douglass Unit Day Crab Feast Car and Bike Show in Easton

    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 […]

  • Simpatico Welcomes Giuliano Hazan for Cooking Classes in St. Michaels

    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, […]