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 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 […]

  • 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 […]

  • Spring Vendor Market In Cambridge

    Join on April 6th from 9am- 1pm Lots of vendors including Scentsy, tastefully simple, thirty one, Tupperware, paintings, jewelry, tumblers, wreaths, leather goods, signs, cupcakes, country decor, handmade items, candles, bath salts and lots more. The Auxiliary will also be serving breakfast and lunch during the Event. Hope to see you there. Please come out […]

  • 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 on this free event for the whole family, with live raptor programs, kids’ activities, refuge tours, exhibits, and more! Call 410-228-2677 for more information or […]

  • 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. This in-person event promises to be a shell of a good time. Don't miss out! In addition to oysters, we will have hamburgers and hot […]

  • St. Patrick’s Day Karaoke at Old Salty’s Restaurant

    Chuckie Hayward will be at Old Salty's Restaurant celebrating St. Patrick's day with karaoke! Stay tuned for drink and food specials to be posted on their Facebook Page. Date and Time Saturday Mar 16, 2024 7:00 PM - 11:00 PM EDT Location Old Salty's Restaurant 2560 Hoopers Island Road Fishing Creek, MD 21634 Website http://ww.oldsaltys.com […]

  • RAR Brew & Irish Stew St. Day The Local Way In Cambridge

    Introducing a pop up event you won’t want to miss-our RAR BREW & IRISH STEW DRIVE THRU!!!!! RAR has sent over some of their Leprechaun Bait Out of Order cans (maybe the most popular can of the season) and we’re ready to pair it with some HOMEMADE Irish beef stew cooked up the Emily’s way!!! […]

  • Adult Easter Egg Hunt 2024

    Join in the fun at Layton's Chance! This adult only Easter Egg hunt is a twist on the traditional hunt! At 6:00pm blindfolded teams of 2 will compete during fun and goofy ways to find hidden eggs. Entertainment, prizes, and of course lots of laughs will fill this evening! After the hunt there will be […]

  • The Eastern Shore Sea Glass and Coastal Arts Festival

    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 […]

  • Cambridge Craft Market and Food Drive

    Blue Ruin is teaming up with One Mission Cambridge to host the Cambridge Craft Market and Food Drive! From 3pm to 9pm on Friday, April 26th, visit Blue Ruin’s parking lot and show room at 400 Race St to shop from over twenty vendors. There will be something for the whole family, from sweets to […]

  • Cambridge Traditional Crab Run

    We are excited to say that we are returning for our traditional Sunday (Mother's Day) event!!! The Crab Run consists of a half marathon (13.1 miles) immediately followed by a 5k (3.1 miles) run, all from the grounds of Great Marsh Park, located at 0 Somerset Avenue, Cambridge. THE HALF MARATHON COURSE IS NORMALLY AN […]