Events on Maryland’s Eastern Shore

Name: St. Michaels Wine Tasting Crawl
Start: 2024-04-27T00:00:00-04:00
End: 2024-04-27T23:59:59-04:00

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.

Talbot County

April 2024
Annual Multicultural Festival in Easton

April 9, 2024 @ 10:00 am - May 4, 2024 @ 2:00 pm

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, […]
Spring Paint & Sip

April 9, 2024 @ 6:30 pm - April 27, 2024 @ 5:00 pm

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 […]
Sip | Savor | Shop

April 11, 2024 @ 4:00 pm - May 31, 2024 @ 6:00 pm

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 […]
Kent Narrows Boat Expo

April 12, 2024 @ 10:00 am - April 26, 2024 @ 5:00 pm

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 […]
Chesapeake Bay Week Film Festival: “Water’s Edge: Black Watermen of the Chesapeake”

April 18, 2024 @ 5:30 pm - 9:00 pm

Celebrate the 20th anniversary of Chesapeake Bay Week with a special film festival, presented by CBMM in collaboration with Maryland Public Television. Dive deep into the Bay's rich history through […]
Tequila and Tulips

April 19, 2024 @ 8:00 am - 6:00 pm

Vintage Family Farms and Corah's Corner are teaming up again to bring you a create your own Tulip bouquet bar with our own field grown Tulips and your favorite Tequila […]
The Eastern Shore Sea Glass and Coastal Arts Festival

April 20, 2024 @ 10:00 am - April 21, 2024 @ 5:00 pm

The Eastern Shore Sea Glass and Coastal Arts Festival brings artisans and craftspeople who will exhibit and sell coastal and sea-glass related jewelry, home décor, art, and more. The popular […]
Beer & Beef Festival at Eastern Shore Brewing Co. In Easton

April 20, 2024 @ 12:00 pm - 5:00 pm

Event by Big Mack’s Kitchen Venue Eastern Shore Brewing https://www.facebook.com/easternshorebrewing
Chesapeake Bay And Maryland Eastern Shore Bike Tour

April 23, 2024 @ 12:00 am - April 26, 2024 @ 11:30 pm

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 […]
Talbot County Day

April 25, 2024 @ 8:00 am - 5:00 pm

Join us on the Talbot County Courthouse Lawn on April 25th, 2024 at 5PM as we celebrate the birthday of Talbot County. This special birthday celebration will include music from […]
Movie Night at The Ebenezer Theater: Hidalgo

April 26, 2024 @ 7:30 pm - 9:30 pm

Hidalgo is an epic biographical film based on the legend of the American distance rider Frank Hopkins and his mustang Hidalgo racing in 19th century Arabia against Bedouins riding pure-blooded […]
St. Michaels Wine Tasting Crawl

April 27, 2024

Uniquely arrive in charming St. Michaels, Maryland by boat! Depart from @kentmorrmarina and enjoy light appetizers with beautiful views to St. Michaels harbor, enjoy the Wine tasting crawl and re […]