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 - Photo by Jill Jasuta

Ongoing Seasonal Attractions

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 11th 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 (weather permitting). Located in the Craig’s Drug Store parking lot, Race and Gay Streets in Cambridge, MD.

Christmas Train Garden - Cambridge - For 90 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.  For information about Train Garden sponsorship or group tours, email conductor@rfctraingarden.org.

Christmas Train Garden - Eldorado-Brookview
Dec. 20, Dec. 21, Dec. 28, Jan. 4
See the Eldorado-Brookview Volunteer Fire Department's Christmas Train Garden on the following dates, from 6:30pm to 8:30pm: Dec. 20 (with Santa!), Dec. 21 (with Santa!), Dec. 28, Jan. 4. There will be a variety of baked goods for sale and a hot cocoa bar. EBVFD Christmas ornaments for sale, too. 5752 Rhodesdale-Eldorado Rd, Eldorado.

Ice Skating in a Winter Wonderland
Nov. 30-Feb. 28, 2025 (See below for dates)
The Hyatt Regency Chesapeake Bay Resort and Blackwater Adventures host a winter wonderland complete with its first-ever synthetic ice skating rink. Enjoy hot chocolate, festive cocktails, s'mores roasting, and shopping from local vendors. Perfect for a family outing or a romantic date night. Open Thursday and Friday, 4-9pm; Saturday 12-9pm; Sunday 12-5pm. Closed Christmas Eve and Christmas Day. Dec. 26-31: 1-9pm. Skates will be available to rent! Santa and Mrs. Claus will be on hand Dec. 20 at 5pm, Dec. 21 at 2pm, Dec. 22 at 4pm. Skating costs $15 per person (10 and older); $10 for children under 10). Ice skates available for rent. Keep up with the latest wonderland updates on the Blackwater Adventures Facebook and Instagram.

Nativity Scenes From Around the World
Dec. 18, 22, and 29; Jan. 5; between 2 and 5pm
Cambridge House Bed & Breakfast hosts a display of Nativity scenes from around the world. Reserve at 410-221-7700.

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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! Downtown Cambridge's Shop 'Til You Drop promotion begins Fri; goes til Dec. 15. For every $25 you spend at participating location, you'll earn chance to win Cambridge Main Street gift basket.  See our listing of shops. 

SPECIAL SHOPPING OPPORTUNITIES AND EVENTS

 All That Glitters 2024: A Metalsmith Collective
Nov. 1-March 1, 2025
Main Street Gallery showcases the jewelry and artwork of seven Eastern Shore metalsmiths (including Wanda Jester, whose work is pictured here). This holiday show features a showcase of the artists’ creative and original jewelry and art glass as well as the artwork of the gallery’s eight member artists. The public is welcome to free Second Saturday receptions Nov. 9 and  Dec. 14 from 5-8 pm. 518 Poplar St., Cambridge.

Santa Storytime
Dec. 18, 10:30am, Cambridge
Join the Dorchester County Library for a visit from Mr. And Mrs. Claus at both branches.

Holiday Bazaar
Dec. 21, 10am-2pm
North Dorchester High School hosts a Holiday Bazaar with local vendors including 21, Blackwater Barista, J.B. Crunch, DCTC Culinary Arts Program and more. Music by the North Dorchester Jazz Band.

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Cambridge Dorchester Christmas Parade - Photo by Jill Jasuta

Ho-Ho-Holiday Fun, Santa Sightings & Festivities

Santa Breakfast at the Hyatt
Dec. 21, 7a-12p
Join the Hyatt for breakfast and visit with Santa at Water’s Edge Grill! Enjoy a delicious breakfast from the Water’s Edge Grill breakfast menu, and see Santa as he walks around the restaurant. $27 for adults, age 5-12 pay their age, 4 and under free. Reservations recommended: 410-901-6400.

Santa in the Neck District
Dec. 21 and Dec. 22
Santa will make his annual visit to the Neck District to visit all of his friends. Chief Webster will be driving him around to visit the children on Saturday Dec. 21 and Sunday Dec. 22 beginning around 6pm. On Dec. 21 after his ride on the engine, Santa will be arriving at the Neck District Volunteer Fire Co. Station around 7:30pm for milk and cookies. Stop by and visit the big guy and get your pictures taken and your bellies full.

Luminaria Celebration in Vienna
December 21, 5-8pm
1,500 luminaria line the streets of the charming, 300-year-old waterfront town of Vienna. Ride the free tram, visit with Santa, and find treats and see the historic button factory at the Vienna Heritage Museum. Several homes will be open to visitors with house tour tickets ($5 per person; children under 6 free); buy tickets that night at the Vienna Heritage Museum, 303 Race St. More information at 410-376-3445.

Ugly Sweater & Hottest Elf Party
Dec. 21, 9:30pm
Johny's Tavern in East New Market hosts some holiday fun with their "Eat, Drink and Be Ugly" Sweater Party and Hottest Elf Party. With DJ Bones.

Kids Christmas Karaoke
Dec. 22, 3-5pm
Johnny's Tavern in East New Market hosts a Christmas karaoke for kids, featuring a special visit from Santa Claus. Let your little ones sing their favorite holiday tunes and meet Santa.

Christmas Eve Walk with Harriet Tubman Museum
Dec. 24, 3-6pm
The Harriet Tubman Museum and Education Center leads a walk from Mount Pleasant Cemetery to Choptank Landing (both sites along the Harriet Tubman Byway), to honor Harriet Tubman, who led her third rescue mission on Christmas Eve, 1854. There will be a musical presentation at the cemetery and a lotus flower release ceremony at the landing. $40 donation per adult children free. Register.

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Wreath Making at Simmons Center Market in Cambridge. Photo courtesy of Simmons.

Crafting and Hands-On Holiday Fun

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

Toddler Ornament Making & Santa
Dec. 19, 10a-12p
Cabin Fever Play Centre offers the chance to make a special ornament with your toddler, and visit with Santa. Ticket includes Admission to Play, ornament supplies, lunch, and a visit with Santa. Buy tickets.

Holiday Ornament Paint Night at the Hurlock Library
Dec. 19, 5:30pm
Pick out a wooden ornament, paint, and enjoy light refreshments at the Hurlock Public Library.

Holiday Crafting Sessions at Prodigal Creations
Throughout the season
Prodigal Creations has several holiday crafting sessions planned for the season for all ages, from Christmas crab resin to seagrass trees to old-time Christmas ceramic trees. See the line-up. They also have projects that you can create; no appointment needed.

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Where to Find Live Christmas Trees & Greens

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

• Chesapeake Seed & Feed in Cambridge has fresh Christmas wreaths and garlands hand created by a local farm; 10% of all sales will be donated to Pleasant Day Medical Day Care.

• Mowbray's Garden Center in Cambridge has trees, plus poinsettias, Christmas cactus, and more. 3009 Old Route 50, Cambridge.

• Mark's Mulch usually 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 - Photo courtesy Dorchester Santa

Giving Back & Sharing Holiday Cheer

Pet Supply Drive by Dorchester County Tourism
Through Jan. 30, 2025
In memory of one of the Dorchester Visitor Center's most frequent guests, Millie (2006-2023), Dorchester Tourism is holding a drive for pet supplies until Jan. 30. Bring pet food, bedding, blankets, towels, toys, or treats to the visitor center during regular hours (Monday-Friday 8:30am-4:30pm; Saturday-Sunday 10am-2pm). Benefits Baywater Animal Rescue and Dorchester County Dog Control. Questions? Call 410-228-1000.

Covered Kids Books & Blankets Drive
Dec. 11-Jan. 2, 2025
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.

New Year's Eve and New Year's Day Festivities

NYE Kids Ball Drop
Dec. 31, 5-8pm
This is a fun event for the entire family, without staying up until midnight! The Ball Drop, (with over 500 balloons, confetti poppers, and more) will be at 7pm, so be sure to arrive before then. Tickets per child are $20 each. 2 adults are free per family. Additional adults are $10. This event usually sells out. Tickets required. Tickets are non-refundable. Buy tickets.

New Year's Eve Party at Blue Ruin
Dec. 31, Seating begins at 5pm
A night of culinary delight, sparkling celebration, and live entertainment. Six-course meal, champagne toast. Plus the debut of The Showroom, Blue Ruin's new music venue. Limited seats available. Reserve your spot online. For more info, contact Blue Ruin at (410) 995-7559. info@blueruinbar.com.

NYE Basket Drops
Dec. 31, 9pm and 12am
Watch some magic happen at Cambridge's Crab Basket Tree on New Year's Eve with two basket drops! Family-friendly celebrations. Music from 96.7 WCEI from 7:#0 to 9pm. The first drop happens at 9pm. Then the second drop happens at midnight. Main Street will be set up with some NYE staples … hats, horns and a selfie station! The Crab Basket Tree – constructed by volunteers out of 200 bushel baskets used for crabbing – is located in the parking lot at Craig's Drug Store, 409 Race St., Cambridge, MD.

New Year's Eve in the Neck
Dec. 31, 7:30pm
Neck District Volunteer Fire Co. hosts a New Year's Eve party Dec. 31 with food, DJ, dancing and singing, champagne toast. BYOB. $50 per person. Buy tickets in advance through their Facebook page, email neckdistrictvfc@gmail.com, or mail check to 954 Cooks Point Rd., Cambridge, MD 21613.

New Year's Eve at the Hyatt
Dec. 31
Ring in the New Year at Hyatt Regency Chesapeake Bay with family-friendly activities. For Hyatt overnight guests only. Find out more.

First Day Hike
Jan. 1, 10am
Join Park Rangers at Harriet Tubman Underground Railroad State Park and Visitor Center in Church Creek to begin a flat and paved 2.5-mile hike into the Blackwater National Wildlife Refuge on their Wildlife Drive. Walk along the Blackwater River and immerse yourself in the beautiful landscape that helped shape Harriet Tubman. All are welcome. No registration required. Details.

Something else to look forward to in January!

Cambridge Ice & Oyster Festival
Jan. 17-18, 2025
Cambridge extends the fun into January with the Cambridge Ice & Oyster Festival, which features dozens of ice sculptures, master ice carver demonstrations, interactive ice games, oyster roast and raw bar, live music, ice bars with craft beer and artisan cocktails, and fire pits and s’mores stations! More info.