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.
VALENTINE'S DAY 2024 NOW OPEN FOR BOOKINGNew this year: We are partnering with Tiger Lily for the ultimate Valentine's experience! Have a romantic carriage ride around Easton followed by dinner ON US at Tiger Lily! Riding and Driving lessons can be booked by clicking BOOK NOW. Please email [email protected] or text 540-460-2455 for private rentals and driving lessons. […]
Hosted by: Classic Motor Museum St Michaels Where: 102 E. Marengo Street, St. Michaels Maryland. When: Every Saturday Morning 9 am to 11 am. From now through the end of March we have […]
Join us every Saturday and Sunday at The Fool's Lantern for brunch and our Build-Your-Own Bloody Mary/Maria Bar! Choose from a variety of vodka or tequila, add our house made […]
top by Simpatico's Courtyard or in the Shop at 104-106 Railroad Ave, just off Talbot Street, every weekend for free tastings of our hand-picked Italian wines! Peruse the shop and […]
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, from 10 a.m. to 2 p.m. A springtime favorite for 24 years on the Mid-Shore, the event celebrates the various cultures contributing to the rich […]
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 host a Spring Sip & Paint session on Saturday, April 27th. Tickets: $40 Event by Far Eastern Shore Winery Venue: 8370 Ocean Gateway, Easton, MD, United […]
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 aged Graviera and Kefalotyri, complemented by an exquisite selection of Mediterranean olives, traditional Greek spreads. Sip and savor the complexity of Greek wines, each bottle […]
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 Deck and the Hyatt Place Kent Island. No cost to enter and no cost to park. Crab Deck is open during the event with […]
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 , gorgeous scenery, sumptuous seafood, boutique shops, and classic bayside towns from the 1600s. Explore at your own pace with our SAG wagon always nearby […]
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 local community groups, a keynote speaker, and of course, birthday cake! During the ceremony, we will also highlight the nominees for the Talbot Citizen and […]
Free Community Event. Food Trucks, Live Music, Emergency Equipment, Non-Profit Booths, Vendor Fair, and more! Venue: Centreville Middle School Event by Thomas Hayman and Centreville Middle School
VIP WineFest 2024 We are pleased to announce WineFest 2024! We are bringing back WineFest 2024. Wine will be tasted from many countries around the world! Wine will be poured, memories will be made and you may just leave with a new favorite! This VIP event will be held at the Old Brick Inn in […]
