Events on Maryland’s Eastern Shore

Name: Plein Air Easton (PAE)
Start: 2026-07-09T00:00:00-04:00
End: 2026-07-19T23:59:59-04:00
Location: Waterfowl Headquarters (40 S Harrison St.)

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

August 2024
Pinot on the Patio in St. Michaels

August 23, 2024 @ 5:00 pm - August 24, 2024 @ 10:00 pm

Join us for a weekend of everything Pinot! Friday night - a multi-course dinner by Stephanie Cook, chef and owner of Wonderment Wines. Saturday - enjoy an afternoon tasting on […]
Clipper ship Pride of Baltimore II In Cambridge

August 31, 2024 @ 8:00 am - September 2, 2024 @ 5:00 pm

Head to Cambridge, Md. Labor Day weekend to see the glorious replica clipper ship Pride of Baltimore II. Dock tours, day sails, sunset sails, Aug. 31 to Sept. 2. Details. […]
September 2024
Skipjack Race & Festival

September 1, 2024 @ 9:30 am - September 2, 2024 @ 5:00 pm

Festival Grounds includes Food Vendors, Arts & Crafts Vendors, Heritage & Education Exhibits and free Children's Activities, both Sunday and Monday The Deal Island (Md.) Skipjack Races happen on Labor […]
Labor Day Parade in Grasonville

September 2, 2024 @ 10:00 am - 3:30 pm

Event by Grasonville Community Center Grasonville Community Center Monday September 2nd 5601 Main Street, Grasonville MD Parade starts at 12pmLine up starts at 10am Following the parade there will be […]
Emily’s Produce Harvest Celebration in Cambridge

September 7, 2024 @ 10:00 am - September 8, 2024 @ 3:30 pm

Who's ready for Fall on the farm?? WE ARE!! Come kick start your Fall season with us at our Harvest Celebration-it's the OFFICIAL start of Autumn at Emily's and the […]
Councell Farms Opening Day near Easton

September 10, 2024 @ 9:30 am - October 30, 2024 @ 5:30 pm

Councell Farms Opening Day! Come visit the Field of Fun, market and get our farm fresh ice cream! Open daily 9:30-5:30 until October 30th. Event by Councell Farms Venue: 11773 […]
Annual End of Summer Crab, Bull, and Oyster Roast In Grasonville

September 21, 2024 @ 10:00 am - 3:30 pm

Join us for our annual End of Summer Crab, Bull, and Oyster Roast! Enjoy crabs, oysters, pit beef, pulled pork, corn on the cob, coleslaw, domestic beer, wine, and seltzers, […]
5th Annual EycktoberFest in Queenstown

September 21, 2024 @ 12:00 pm - 10:30 pm

Join us for our 5th Annual EycktoberFest! YOU have made this event our favorite every year! German-inspired eats by Field Kitchen! Games of skill including the Stein Hoist, Hammerschlagen and […]
October 2024
The Addams Family (1993) – Outdoor Movie Night at The Academy Art Museum

October 4, 2024 @ 8:00 am - 10:00 pm

They're creepy and they're kooky. Mysterious and spooky. They're all together ooky...come and see The Addams Family! Bring a chair and a blanket for cinema under the stars! Our movie […]
Easton’s Fall Kickoff Weekend

October 4, 2024 @ 10:00 am - October 5, 2024 @ 9:30 pm

Event by Discover Easton Venue: 11 S Harrison St, Easton, MD, United States, Maryland 21601 Autumnal decorations and the feeling of seasonal warmth will be all around downtown Easton for […]
June 2026
Chesapeake Chamber Music Festival

June 12 - June 20

Ebenezer Theater

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 […]
July 2026
Plein Air Easton (PAE)

July 9 - July 19

Waterfowl Headquarters (40 S Harrison St.)

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? […]