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.
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3 events,
MUSIC BINGO - Free to play, Prizes to win! No ticket required, first-come, first-served. Possession of a ticket does not guarantee a seat at the gameshow. Contact the venue to discuss best time to arrive to get a seat. Play That Funky Bingo is like regular bingo but instead of calling numbers, we play parts of songs. […] 
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. […] 
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 […] |
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4 events,
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About this event Sunday, February 4 · 12 - 1:30pm EST 1 hour 30 minutes Mobile eTicket Valentine's Cookie Class Join us for a fun and delicious Valentine's Cookie Class at Carrie Sue’s CupCakery! Get your hands dirty and learn the art of decorating cookies with our Brandy from Shore Good Cookies. This in-person event will […] |
6 events,
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About this event 2 hours Mobile eTicket $15-20 per ticket What better way to celebrate Valentine's weekend than spending it with the little ones that you love. Join us for a fun morning filled with great food, fun crafts, family-friendly games, and more. Date and time Saturday, February 10 · 11am - 1pm EST Location […]
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About this event 5 hours 30 minutes Mobile eTicket $50-75 per ticket come out and enjoy yourselves with some live music good vides with a prom theme and setting with a red carpet that meets you to your car with a photographer waiting to flick you up as well as proformances by Ms Ayla Dennis […]
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Join us for an unforgettable dining experience at Layton’s Chance Vineyard & Winery. Indulge in a delectable culinary journey prepared by our talented chef Chris, showcasing the finest ingredients and flavors. Immerse yourself in the cozy ambiance of the vineyard, surrounded by breathtaking views and the soothing sounds of nature. Savor each bite as you […] |
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4 events,
Chesapeake Fire & Ice Festival Returns to Easton, MD in 2024! Larger-than-life sculptures made of solid ice will be on display throughout the historic downtown! Festival will feature dozens of ice sculptures throughout Easton’s Historic District. Friday nights kick off will feature live ice carvings, music, and restaurant specials. The celebration will offer free live […] |
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7 events,
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 a "Coffee in the Barn" event every Saturday. This happens directly in the museum barn. It is free for members and $5 for non-members. It […] 
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 mix, and then choose from over 20 toppings to create your unique drink. Pair it with items from our brunch menu to start your weekends […] 
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 chat with our enthusiastic staff - We Love All Things Italian! We also offer free tastings all week long. Salute!
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St. Michaels ChocolateFest will be held March 2, 2024 and will include restaurant chefs conjuring up amazing delectable special menu items to showcase chocolate inspired dishes and desserts. The Chocolate Crawl will take place on Saturday, March 2, 2024 from 11:00 a.m. - 4:00 p.m. until sold out throughout the Town of St. Michaels at participating businesses […] |
