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.

Looking for events near your rental? Browse vacation rentals by town.

  • 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 […]

  • 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 […]

  • 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 […]

  • 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 […]

  • The Famous Annapolis City fireworks from the Water

    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 […]

  • 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!!! […]

  • 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, […]