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.
The Eastern Shore Sea Glass & Coastal Arts Festival will celebrate it's 16th Annual Spring Edition on the beautiful waterfront campus of the Chesapeake Bay Maritime Museum in St. Michaels on April 18-19, 2026 and offers fun for the whole family with fantastic shopping, great food and drinks, live music on two stages, and more. […]
🎨✨ Paint the Town: Art Show & Sale ✨🎨 Get ready to celebrate creativity at Paint the Town, our exciting art show and sale featuring local artists! Discover vibrant paintings, […]
🌸 𝐁𝐥𝐨𝐨𝐦 & 𝐁𝐫𝐮𝐧𝐜𝐡🌸 𝐎𝐮𝐫 𝐌𝐨𝐭𝐡𝐞𝐫’𝐬 𝐃𝐚𝐲 𝐂𝐫𝐞𝐚𝐭𝐢𝐯𝐞 𝐁𝐫𝐮𝐧𝐜𝐡 𝐢𝐬 𝐛𝐚𝐜𝐤 If you’re looking for something meaningful (and not just another crowded restaurant brunch), this is it. Join us at […]
Bring a touch of seaside charm into your home! In this relaxing and creative workshop, you’ll learn the art of mixing, pouring, and layering resin to create stunning ocean wave […]
Where Artists, Audiences, and Acoustics Come Together in Downtown Easton, Maryland! The Chesapeake Chamber Music Festival, now in its 41st year, is held over the course of two-weeks each June […]
When is Plein Air Easton? The annual competition is held in Easton, Maryland, each July. 2026 Plein Air Easton is planned for July 10-19, 2026. What is Plein Air Easton? […]
Talbot County has found itself starring on the big screen from time to time, but this Oct. 8-10, 2026 the film industry becomes the star in Talbot County as it […]
