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.
On Saturday and Sunday, the prestigious juried exhibit draws a wide selection of regional collectors as well as from major cities along the Eastern Seaboard. The much-anticipated annual show is well known throughout the area and celebrated as the season’s “kick-off” for art lovers. The exhibit featuring 36 artists from the mid-atlantic region and beyondis […]
Come out to the Jetty Restaurant and Dock bar for amazing food and the best drinks in the area! Enjoy the beautiful view and if you are feeling the vibes […]
The CMM is proud to bring our community together in honoring the service of our military heroes by hosting the Annual Classic Motor Museum Parade. The participants will line up […]
Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew. Advance […]
Come sail away with Kalmar Nyckel for a 2.5-hour sail and have an adventure of a lifetime! The Tall Ship of Delaware returns to Cambridge, MD on Friday, June 2 […]
Looking to go sailing at sunset while sipping champagne? This is the sunset champagne charter for you! Come join us for a relaxing 2 hour cruise near Annapolis. Your St […]
Come sail away with Kalmar Nyckel for a 2.5-hour sail and have an adventure of a lifetime! The Tall Ship of Delaware returns to Cambridge, MD on Friday, June 2 […]
Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew. Advance […]
On June 3rd, from 12:00 pm - 4:00 pm come out to the St. Michaels Brewfest 2023! They offer Three Pouring Venues, Over A Dozen Breweries, Art, Glassware, Food, and […]
With over 6,000 people in attendance, 2019 launched the Inaugural Annapolis Pride Parade & Festival– a visual dreamscape of the human spirit at its best. People, children, and pets of every […]
Come sail away with Kalmar Nyckel for a 2.5-hour sail and have an adventure of a lifetime! The Tall Ship of Delaware returns to Cambridge, MD on Friday, June 2 […]
Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew. Advance […]
