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.

  • Easton Carriage Tours

    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. […]

  • Far Eastern Shore Winery’s – Sip and Stitch Sundays

    About this event Far Eastern Shore Winery invites you to join us for our Sip & Stitch Sundays series. We’ve had so much fun the past two Sip & Stitch Events over Halloween weekend and, more recently, on Small Biz Saturday, we thought we’d try to grow our stitching network. We’ll be hosting informal crochet […]

  • Cars and Coffee in the Barn Classic Motor Museum Saturdays

    Motor Museum 102 E. Marengo Street, St. Michaels, MD, United States

    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 […]

  • Build-Your-Own Bloody Mary/Maria Bar at The Fool’s Lantern

    The Fool's Lantern 310 S. Talbot St., St.Michaels, MD, United States

    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 […]

  • Simpatico Free Wine Tasting Events Every Weekend

    Simpatico 104-106 Railroad Ave, St.Michaels, MD, United States

    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 […]

  • Opening day at Scottish Highland Creamery

    Opening day at Scottish Highland Creamery from 3:00 pm to 8:00 pm. Face painting 3:00 – 5:00, new ice cream flavors, special prize for 1st customer of the season! DETAILS […]

  • St. Pat’s Karaoke Night @ Lil’ Bitta Bull

    Join Leprechaun Lucky Chuckie as we kick off St. Patrick's weekend! Friday Night Karaoke starts at 9 p.m. at Lil' Bitta Bull BBQ and going until... $5 Lucky Shots all night! Kitchen […]

  • 20th Annual Eagle Festival

    The 20th Annual Eagle Festival at Blackwater National Wildlife Refuge on Saturday, March 16, 2024, from 9:00 a.m. to 4:00 p.m. as we celebrate birds of prey! Don’t miss out […]

  • Candle Light Cove’s Spring Festival

    Candle Light Cove 106 W Earle Ave, Easton, MD, United States

    About the eventCandle Light Cove's Spring Festival Open to the public! Free event! Community partner festival/yard sale, shop from local vendors, Easter Bunny, Food Trucks, Peep Show Voting & Winners […]

  • Cambridge Rotary Community Foundation Oyster Festival

    Join us for a shuckin' good time at the Cambridge Rotary Community Foundation Oyster Roast! Indulge in delicious oysters, mingle with fellow oyster enthusiasts, and support a great community organization. […]