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. No wonder Cambridge was named one of the “Top 12 Christmas Towns” by Only in Your State for 2021! And one of “8 Charming Towns In Maryland That Could Star In A Hallmark Christmas Movie!” By TravelAwaits.

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. Also note that the Hyatt Regency Chesapeake Bay Resort features family-friendly holiday activities Dec. 20-31, from cookie decorating to hay rides.

Where to Stay

Ongoing Seasonal Attractions

Bushel Basket Tree in Vienna, MD - Photo by Ellen WheatleyCrab Basket Christmas Trees  – Dorchester County is now home to two Christmas trees built out of bushel baskets used for crabbing (crabs are big around here)! First, there’s Cambridge’s Crab Basket Tree, a tradition that began seven years ago and 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. A more recent addition is the Crab Basket Tree in Vienna, MD. Now in its second year, it’s created from some 150 bushel baskets and is located at Vienna’s Entrance Park, located at Gay Street and Old Ocean Gateway.

Christmas Train Garden, Cambridge, MDChristmas Train Garden – For 87 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! This year’s themes include “Train Gardens of the Past” and the “Harvesters at the Holidays” display honoring Dorchester County’s heritage of bountiful seafood and farming production. Free admission, but donations are welcome. The display is open for inside viewing throughout December: Monday through Friday, 6-9pm and Saturday and Sunday 1-4pm and 6-9pm. Closed Christmas Day. Best to check their Facebook page before visiting for any last-minute updates. 307 Gay St., Cambridge, MD.

Nativity Scenes From Around the World
2-5pm, Wednesdays and Sundays, Dec. 1-Jan. 5
Cambridge House Bed & Breakfast hosts a display of Nativity scenes from around the world. $10 per person; reserve at 410-221-7700.


Shopping and Unique Gifts

Dorchester County is all about great indie (independently owned) shops. Antiques, vintage, upcycled furniture, artist and artisan-created works of all kinds, fine jewelry, Eastern Shore and Maryland-themed items, toys and clothes for the wee ones, women’s apparel and accessories, home and garden decor, and more! All with the attention and friendliness of shop owners. See our listing of shops

Where to Shop

Earrings by Linda Starling at Main Street Gallery, Cambridge, MD

‘Bright and Beautiful’ at Main Street Gallery – Browse distinctive works of art from local artists at this gallery in Downtown Cambridge now through December. The show is “Bright and Beautiful,” and features smaller works of art for gift giving. The show runs Nov. 4 through Jan. 2.

New Year’s Eve

NOTE: While there won’t be the traditional workboat drop this year at midnight in Downtown Cambridge, Blue Ruin has stepped up and will have their New Year’s Eve ball drop in front of their building at the corner of Gay and Race Streets for all to enjoy.

New Year’s Eve Kids Ball Drop – Cabin Fever Play Centre hosts an early ball drop for the younger set, 5-8pm. This is a ticket-only event.

James Bond New Year’s Eve Party – Blue Ruin hosts a four-course dinner (must reserve in advance) followed by a party, live music, and ball drop.

New Year’s Eve at the Hyatt Chesapeake – New Year’s Eve party with live music DJ, live feed from NYC, adult champagne toast, kids sparkling cider toast, family balloon drop and party favors, and more.

New Year’s Eve at Maryland Blue – The Line Bar at Maryland Blue has live music with the Wyes Guys and more.

New Year’s Eve in the Neck – Neck District Volunteer Fire Co. hosts a New Year’s Eve party Dec. 31 with appetizers, dinner, music, dancing, and a toast at midnight.

Fat Ricky’s A Toast to the New Year Celebration – Live music with Twisted Fate, party favors, and champagne toast; special dinner menu available, too.

Johnny’s Tavern New Year’s Eve Dinner & Party – Special dinner followed by a party with drink specials, music, and more.

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

Live Jazz at LabRARtory – RAR Brewing hosts a jazz ensemble from Louis Pettinelli at their LabRARtory, 7-11pm.

Find details on all these happenings on our online calendar!

Events Calendar


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