Attractions  |  Events  |  Shopping  |  Crafting  |  Live Trees & Greens  |  Giving Back

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, has been featured as 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.

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. Now in its 10th year, 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 the day after Thanksgiving. Located in the Craig’s Drug Store parking lot, Race and Gay Streets in Cambridge, MD. (Stop into Craig’s for the official Crab Basket Tree Ornament!)

Christmas Train Garden – For 89 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. From Dec. 1 until Dec. 31, open Monday through Friday 6-9pm; Saturday and Sunday 1-4pm and 6-9pm. Closed Christmas Day. For the latest updates, check their Facebook page. 307 Gay St., Cambridge, MD. Also, take part in the Lego Brick-Off – enter your favorite Lego holiday-themed creation to be on display at the Train Garden for the month of December. Details.

Nativity Scenes From Around the World
Wednesdays and Sundays, Dec. 3 through Jan. 7, 2024
Cambridge House Bed & Breakfast hosts a display of Nativity scenes from around the world between 2 and 5pm, Wednesdays and Sundays. Reserve at 410-221-7700.

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Cambridge Dorchester Christmas Parade - Photo by Jill Jasuta

Cambridge Dorchester Christmas Parade – Photo by Jill Jasuta

Ho-Ho-Holiday Fun, Santa Sightings & Festivities

Harriet Tubman Christmas Eve Walk
Dec. 24, 3-6pm
The Harriet Tubman Museum & Education Center leads a special 3.5-mile walk tracing the footsteps of Tubman’s 1854 Christmas rescue. Ken Johnston, Linda Harris, and David Cole guide you on a journey of history, code songs, and storytelling from the banks of the Choptank River. Admission $35 adults; $15 children. Benefits the museum.  Reserve here.

Little Whisks Culinary School: Sugar Cookies & Decoration
Dec. 27, 10am
Mandala Pies Bakery in Vienna hosts a workshop for the young ones to bake sugar cookies from scratch and them decorate them. Adults may stay or drop off for this two-hour workshop. $40 per child ($5 sibling discount). Register by email at caitlin@mandalapies.com.

 

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Sea Glass Trees at Bay Country Shop, Cambridge

Sea Glass Trees at Bay Country Shop, Cambridge. Photo courtesy Bay Country Shop.

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, 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

SPECIAL SHOPPING OPPORTUNITIES AND EVENTS

 

Work by Cindy Ayd at Main Street Gallery, Cambridge, MD

Work by Cindy Ayd at Main Street Gallery

Main Street Gallery: All That Glitters: A Women’s Metalsmith Collective
Nov. 2-Dec. 31
Main Street Gallery showcases the jewelry and artwork of seven Eastern Shore metalsmiths (including Cindy Ayd, whose work is pictured above). The public is welcome to a reception Dec. 9 from 5-8 pm. 518 Poplar St., Cambridge.

The Merry Market at Dorchester Center for the Arts
Nov. 4-Dec. 23
Dorchester Center for the Arts presents its Merry Market, transforming the entire art gallery into a whimsical shopping experience with the work of various artists with jewelry, wreaths, artwork, and more. Free Second Saturday reception December 9, 5-7pm. 321 High St., Cambridge.

 

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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 trees, plus poinsettias, Christmas cactus, and more. 3009 Old Route 50, Cambridge.

• Mark’s Mulch has live trees. 527 Race St., Cambridge.

• Shorelife Home & Gifts is taking orders for fresh, made-to-order holiday 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.

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

Dorchester Santa Toy Drive – Photo courtesy Dorchester Santa

Giving Back & Sharing Holiday Cheer

Covered Kids Books & Blankets Drive
Dec. 11-Jan. 2, 2024
Harvesting Hope Youth and Family Wellness hosts its annual campaign to help local kids. Drop off books and blankets at Harvesting Hope, 204 Cedar St., Cambridge; Dorchester Chamber, 306 High St., Cambridge; or Hurlock Town Hall, 311 Charles St., Hurlock.

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.

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.

Coat Drive
Jones Mini Mart is accepting new or gently used coats for people of all ages and sizes. Store is open 10am-12am. Questions? Call 443-477-6191.

 


New Year's Eve in Dorchester County, Maryland

 

New Year’s Eve and New Year’s Day Festivities

New  Year’s Eve Yoga Party
Dec. 31, 10am-1:30pm
Anahata Yoga in Cambridge hosts its annual NYE paraty with three yoga claasses between 10am and 1:30pm. $20. Register at anahatayogamd.com.

New Year’s Eve at Old Salty’s Restaurant
Dec. 31, 4pm-1am
Buffet 4-8pm at Old Salty’s on Hoopers Island. Ring in the New Year at the after party with Wavvy Gravy, 9pm-1am. Reserve at 410-397-3752.

New Year’s Eve 24K Gold Party at Blue Ruin
Dec. 31, 5pm
Blue Ruin will have two sets of coursed dinners for the evening – reservations required for all parties. The first will be a three-course meal offered from 5-7:30pm, and the second will be a four-course meal with champagne pairing offered between the hours of 7:30-10pm. Watch for menu and pricing information on the Blue Ruin Facebook page. Reserve at paul@blueruinbar.com. Live music at 10pm, followed by their annual lit ball drop on the corner of Race and Poplar Street at the entry to Blue Ruin at midnight.

New Year’s Eve Kid’s Ball Drop
Dec. 31, 5-8pm
Cabin Fever Play Centre hosts a party for the youngsters with party swag, confetti poppers, face painting, and more. $18 per child; adults are free. Tickets required. This one always sells out.

New Year’s Eve in the Neck
Dec. 31, 6:30pm
Doors open at 6:30pm with music and appetizers. Dinner at 8pm with crab cakes, strip steak, chicken Marsala, shrimp Rockefeller, and more. BYOB event, but they will provide champagne for the midnight toast. $45 per person. Space fills fast; reserve here. At the Neck District Volunteer Fire Company.

New Year’s Eve at the Hyatt
Dec.  31
For overnight guests of the Hyatt only.  Enjoy the many family-friendly activities lined up for their NYE celebration, including buffet dinner, obstacle course, inflatable slides, game rooms, and more.  See the rundown of events. Don’t miss their life-size gingerbread house!

New Year’s Eve Club Legacy Reunion
Dec. 31, 7pm
Legacy Entertainment presents a New Year’s party for age 30 and up, hosted by comedian Desi Alexander and feaaturring Bunkey the Strut King. Music, dance-off, food, door prizes, more. $50 in advance. At Minnette Dick Hall, Cambridge. Buy tickets.

First Day Hike
Jan. 1, 9:45am
Join a Maryland Park Service Ranger on a 2-mile guided hike along a portion of Wildlife Drive through Blackwater National Wildlife Refuge. The Wildlife Drive is flat and paved, so it makes for an easier hike. Pets are not permitted in the refuge. Participants should wear weather-appropriate clothing and bring drinking water. Meet at the Entrance to the Harriet Tubman Visitor Center in Church Creek, MD. Arrive by 9:45am; hike begins at 10am. Visitors can explore the Harriet Tubman Underground Railroad Visitor Center after the hike to learn about Harriet Tubman’s life and legacy and/or become Junior Rangers. Pre-register here.


Something else to look forward to in January!

Cambridge Ice & Oyster Festival
Jan. 12-13, 2024
Cambridge extends the fun into January with the Cambridge Ice & Oyster Festival, which features more than 40 ice sculptures, master ice carver demonstrations, interactive ice games, oyster roast and raw bar, ice bars with craft beer and artisan cocktails, fire pits and s’mores stations, and a shucking and slurping oyster contest.

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