Cambridge Classic Powerboat Regatta
The oldest active powerboat race in the country happens right here in Dorchester County, Maryland. This year's race will be held on May 20-21, 2023 on the Choptank River. About […]
12 events found.
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.
Events
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St. Michaels Farmer’s Market (20th)
The St. Michaels Farmers Market features farmers and vendors selling locally grown and caught vegetables, meats, and fish, plus handmade crafts and live music.
Free -
39th Annual Oxford Fine Arts Fair
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 […]
$5 -
Karaoke Night – The Jetty Restaurant and Dock Bar (May 24th)
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 […]
Free -
Classic Motor Museum Memorial Day Parade
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 […]
Free -
Sail on the Skipjack Nathan (May 27th)
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 […]
$40 -
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Tall Ship Kalmar Nyckel Sails in Cambridge (June 2nd)
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 […]
$65 -
Chesapeake Bay Champagne Sunset Sail
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 […]
$115 -
Tall Ship Kalmar Nyckel Sails in Cambridge (June 3rd)
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 […]
$65 -
Sail on the Skipjack Nathan (June 3rd)
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 […]
$40 -
St. Michaels Brewfest 2023
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 […]
$55 – $110 -
Annapolis Pride Parade & Festival
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 […]
Free
