Whether you’re decking the halls, getting crafty, or checking in with Santa … there’s something extra special about the holidays in the Heart of Chesapeake Country. Dorchester County is home to independent shops with great gift ideas and friendly shopkeepers, intriguing art galleries, and excellent restaurants offering indoor, outdoor and take-out dining. Masks and social distancing required. For details, just click on the event name. We’ll be adding to this listing as we find out about more events.

And, if you’re looking for a place to curl up and relax – or need room for visiting friends and family – take advantage of off-season rates at hotels and B&Bs! See our lodging listings.

Events Calendar

Ongoing Seasonal Attractions

Crab Basket Christmas Tree  – Cambridge’s Crab Basket Tree has become one of the Shore’s favorite holiday destinations! Gather round the tree for selfies or just to admire. The tree is constructed by volunteers of nearly 200 crab baskets that were used by watermen for crabbing. Located in the Craig’s Drug Store parking lot, Race and Gay Streets in Cambridge, MD.

Christmas Train Garden – For 86 years, volunteers with the Cambridge Rescue Fire Company have created this spectacular train garden for the holidays. The RFC Train Garden is the longest continually operating fire department train display in the nation! Because of COVID-19, this year it will be an outdoor, socially distanced train garden with limited hours. This year’s theme, The City of Light, features miniature towns, cities, farms, forests, factories and highways, all decked out in holiday revelry, and crisscrossed by model trains. Weather permitting, the display runs Fridays and Saturdays in December from 6 to 8pm and Sundays from 4 to 6pm, with special openings on Christmas Eve and New Year’s Eve. Best to check their Facebook page before visiting. 307 Gay St.

Shopping and Unique Gifts

Don’t miss our Holiday Gift Guide for great ideas for everyone on your list! Shop local!

Gallery of Gifts at DCA

Gallery of Gifts at Dorchester Center for the Arts – This seasonal favorite features an extensive selection of handcrafted items from local and regional artists, perfect for thoughtful gift-giving. You’ll find fiber art, gold and silver jewelry, glass, photography, paintings, and ceramics. Show runs through Dec. 19.

Main Street Gallery – Browse distinctive works of art from local artists at this gallery in Downtown Cambridge now through December. Current show is “Get Away” (remembering happier, beach days) featuring artist Laurie Flannery.




Pick out the perfect tree at Mowbray’s Garden Center, Emily’s Produce (Emily’s offers both in person and delivery), with Mike Diaz (located behind the Dairy Queen), all in Cambridge. Or M&R Christmas Tree Farm in Hurlock. You’ll  also find live wreaths, garlands, poinsettias, and more at Mowbray’s and Emily’s, as well as at Simmons Center Market.

Giving Thanks & Giving Back

Wreaths Across America - Eastern Shore Veterans CemeterySalvation Army – Help them #RescueChristmas. Look for the iconic red kettles either set up outside of stores or smaller kettles on countertops inside shops. Donations help local families struggling with hunger, poverty, or job loss. Call 410-228-2442 x1008 for more info.

Santa Swim and Care and Share Fund – This year’s Santa Swim was canceled because of COVID-19, but you can still donate to the cause to help the Dorchester County’s most vulnerable. Send donations to The Care & Share Fund Inc., P.O. Box 1256, Cambridge, MD 21613.

New Year’s Eve

New Year’s Eve All Day Yoga at Anahata Yoga – Get ready for the New Year with eight opportunities for mindful movement starting at 6am and running all day. Must pre-register.

Kid’s Ball Drop – Cabin Fever Play Centre hosts a ball drop inside their arcade at 7:30pm. Party favors available while supplies last. Limited tickets. $10 per person. 5-8pm, Dec. 31.

New Year’s Eve Boat Drop – Downtown Cambridge hosts a New Year’s Eve Boat Drop with a small replica of a deadrise — the traditional waterman’s workboat — dropping at 8pm on Dec. 31 to bring in the New Year. (It’s earlier than usual since bars and restaurants are currently required to close at 10pm.) 500 block of Poplar Street right near the Crab Basket Tree. The event will also be broadcast live on the Downtown Cambridge Facebook page.

Brazilian New Year’s at Fat Ricky’s – Fat Ricky’s goes Brazilian style by celebrating New Year’s at 9pm instead of midnight. (This is to comply with Gov. Hogan’s 10pm closing rule for bars and restaurants because of COVID-19.) Offering dinner specials with Brazilian dishes, live music, and more. Reservations required.

Vintage 414 – Offering a special tasting menu to go (pre-orders only). Plus in-house dining by reservation with regular menu and tasting menu. See their Facebook post for details.

Blue Ruin  – Offering a special three-course meal with cheese board (thanks to their partners Simmons Center Market, Vintage 414, and Bombay Tadka). Open to only the diners from 7 to 10pm. See their Facebook page for details.

New Year’s Eve with Pete Baker at Canvasback – Canvasback Restaurant and the Dart Bar host musician Pete Baker starting at 6pm.

New Year’s Eve Party at Hoopers Island Volunteer Fire Company – Doors open at 8:30pm. Music by DJ Chuckie Hayward. $10 per person at the door. Bring your own drinks and snacks.

Find details on all these happenings on our online calendar!

Events Calendar

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