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.

Ongoing

Easton Carriage Tours

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. […]

Annual Multicultural Festival in Easton

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 Paint & Sip

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 […]

Sip | Savor | Shop

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 […]

Kent Narrows Boat Expo

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 […]

Chesapeake Bay And Maryland Eastern Shore Bike Tour

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 […]