Holiday Events, Shopping, and Fun with Eastern Shore Flavor!

Whether you’re decking the halls, getting crafty, or checking in with Santa … there’s something special about the holidays in Dorchester County on Maryland’s Eastern Shore. Maybe it’s the small town charm, the laid-back vibe, the warm friendliness, the cool independent shops and galleries, or the fun events. (No wonder our largest city, Cambridge, is one of “8 Charming Towns In Maryland That Could Star In A Hallmark Christmas Movie” from TravelAwaits!)

While you’re here, take in our beautiful nature and great birding, then wrap up the day with scrumptious local crabs or oysters. 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. The Hyatt Regency Chesapeake Bay Resort features family-friendly holiday fun, from dive-in holiday movies to breakfast with Santa. Delmarva residents can save with the offer code DELMAA on their website, or by calling the hotel at 410-901-1234.

For details on anything here, click on the event name. We’ll be adding to this guide as more happenings are announced. Have a holiday event happening in Dorchester County that you’d like to add? Submit it here.

There’s a lot to love during the holiday season here in the Heart of the Chesapeake!


Christmas Train Garden - Cambridge Rescue Fire Company - Dorchester County

Christmas Train Garden – Cambridge Rescue Fire Company – Photo by Jill Jasuta

Ongoing Seasonal Attractions

Crab Basket Christmas Tree_Cambridge, MD - Photo by Jill Jasuta

Crab Basket Christmas Tree in Downtown Cambridge – Photo by Jill Jasuta

The Original 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 who put together nearly 200 crab baskets that were used by watermen for crabbing. Volunteers usually construct the tree in the days after Thanksgiving. Located in the Craig’s Drug Store parking lot, Race and Gay Streets in Cambridge, MD.

Christmas Train Garden – For 88 years, volunteers with the Cambridge Rescue Fire Company have created this spectacular train garden for the holidays – the longest continually operating fire department train display in the nation! The train garden changes each year and features miniature towns, cities, farms, forests, factories and highways, all decked out in holiday revelry, and crisscrossed by model trains. This year’s theme is Hollywood Holiday, with cartoon characters, classic movie scenes, superheroes, and other fun. Dec. 1-Dec. 31: Monday through Friday 6-9pm; Saturday and Sunday 1-4pm and 6-9pm. Closed Christmas Day. For the latest updates, check Facebook page. 307 Gay St., Cambridge, MD.

Nativity Scenes From Around the World
2-5pm, Wednesdays and Sundays, Dec. 4-Jan. 4, 2023
Cambridge House Bed & Breakfast hosts a display of Nativity scenes from around the world. $10 per person; reserve at 410-221-7700.


Cambridge Dorchester Christmas Parade - Photo by Jill Jasuta

Cambridge Dorchester Christmas Parade – Photo by Jill Jasuta


Holiday glassware at Shorelife Home & Gifts, Cambridge, MD

Holiday glassware at Shorelife Home & Gifts, Cambridge, MD – Photo courtesy Shorelife Home & Gits

Shopping and Unique Gifts

Dorchester County is all about great indie (independently owned) shops. All with the helpful attention and friendliness of shop owners. Shops and galleries around Dorchester County have stocked up for the holidays with all kinds of interesting items – some of them created by artists and artisans, some capturing the feel of the Eastern Shore, and others just beautiful in their own right. 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!  See our listing of shops

Where to Shop


Robin Morgan’s “Pendant Honeycomb and Bee - Holiday Show at Main Street Gallery - Cambridge, MD

Robin Morgan’s “Pendant Honeycomb and Bee” – All That Glitters Show at Main Street Gallery

Main Street Gallery: All That Glitters: A Women’s Metalsmith Collective
November 3-December 31
Main Street Gallery showcases the jewelry and artwork of seven Eastern Shore metalsmiths (including Robin Morgan, whose work is pictured above). The public is welcome to a reception December 10 from 5-8 pm.

The Merry Market at Dorchester Center for the Arts
November 4-December 23
Dorchester Center for the Arts presents its new Merry Market, transforming the entire art gallery into a whimsical shopping experience with the work of dozens of artists and their traditional arts and crafts, jewelry, candles and more. Free Second Saturday reception December 10, 5-7pm.






Mistletoe & Mimosas at Layton's Chance Winery

Mistletoe & Mimosas at Layton’s Chance Winery – Photo courtesy Layton’s Chance

Holiday Crafting and Creating

Looking to make handcrafted gifts or something for yourself? Check out the workshops and classes by the Blue Awning, Mowbray’s Garden Center, Phippin’s Crafting Corner, and the Dorchester Center for the Arts. NOTE: Many of these workshops sell out, so reserve your spot as soon as you can!

Holiday Crafting Sessions at Phippin’s Crafting Corner
Phippin’s has several holiday crafting sessions planned for the season for all ages, from a 4-foot snowman porch sign to Santa’s cookies and milk plate to a kids’ reindeer food making night. See the line-up.

Where to Find Live Christmas Trees & Greens

Live trees and greens add that special touch to holiday decorating!

• Mowbray’s Garden Center in Cambridge has live trees. Plus poinsettias, Christmas cactus, and more.

• Mark’s Mulch has live trees, from 5 ft to 14 ft. 527 Race St., Cambridge.

• Shorelife Home & Gifts in Cambridge is taking orders for fresh, made-to-order holiday wreaths – with options including boxwood, magnolia/boxwood and magnolia/boxwood/winterberry wreaths. Stop in at 421 Race St Cambridge or call 443-205-4325.

• Simmons Center Market has poinsettias, Christmas cactus wreaths, greens, and more. 600 Race St., Cambridge.

• M&R Tree Farm in Hurlock offers up you-choose-you-cut or you-choose-they-cut trees such as Colorado Blue Spruce, Douglas Fir, Eastern Red Cedar, Norway Spruce, and White Fir. Open Saturday, December 3 and December 10, 2022, from 10 am to 5 pm. Cash only. 7034 East New Market Ellwood Road, Hurlock, MD; 410-714-3058.


Dorchester Santa Toy Drive - 2021 - Photo courtesy Dorchester SantaDorchester Santa Toy Drive - 2021 - Photo courtesy Dorchester Santa

Dorchester Santa Toy Drive – 2021 – Photo courtesy Dorchester Santa

Giving Back & Sharing Holiday Cheer

Salvation Army
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 x 1008 for more info or donate online.

Christmas for Seniors Drive
The Groove City Black Heritage & Culture Group is sponsoring a Christmas for Seniors Drive. Donations will be used to create gift baskets for Cambridge seniors in nursing homes, Conifer Village and Bradford House. Blankets, slippers, warm socks, PJs, puzzle books, lotion, hat, scarf and glove set. Donation deadline is December 16. Drop-off locations: Chamber of Commerce, 306 High St., Cambridge; Blue Awning, 430 Race St.; Dorchester Visitor Center, 2 Rosehill Pl. All in Cambridge. Details at 443-225-0819 or

Wreaths Across America - Eastern Shore Veterans Cemetery

Wreaths Across America at the Eastern Shore Veterans Cemetery

Pleasant Holidays
Pleasant Day Medical Adult Day Care seeks donations to purchase gifts for their participants, such as clothing, living supplies, and homemade holiday dinners by Tolley’s Catering. There are also raffle prizes. Find out more.

Covered Kids Campaign
Harvesting Hope is collecting new blankets, covers and throws for youth in Dorchester County. Donate online or drop off at 204 Cedar St., Cambridge; Dorchester Chamber at 306 High St., Cambridge; or Town of Hurlock at 311 Charles St., Hurlock.

Find details on all these happenings or browse by date on our online calendar!

Dorchester Events Calendar


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