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.

Ongoing

Easton Music Bingo at Doc’s Downtown Grille

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 […]

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 […]

Pirate & Mermaid Valentine Brunch

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 […]

Endless Vision’s Valentines Gala

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 […]

411 kitchen winter dining experience

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 […]