Catch that Eastern Shore holiday spirit!
JUMP TO:
🟥 Ongoing Seasonal Attractions (Crab Basket Tree, Train Garden, more)
🟥 Shopping Events & Markets
🟥 Holiday Events (parades, Santa visits, more)
🟥 Holiday Crafting
🟥 Live Trees & Greens
🟥 Giving Back
🟥 New Year's Eve & New Year's Day
Dorchester County's small town charm, the laid-back Eastern Shore vibe, the warm friendliness, the cool independent shops and galleries, and the fun events make the holiday season even better.
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 below, 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? Drop us a note at jill@visitdorchester.org.
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 12th 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. Follow the latest and post your photos on the tree's Facebook page.
Christmas Train Garden - Cambridge - For more than 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.
Ice Skating in a Winter Wonderland
Nov. 28, 2025–Feb. 15, 2026
Enjoy an on-site synthetic ice-skating rink and Winter Village at the Hyatt Chesapeake Resort, open Thursdays through Sundays throughout the winter season, with extended hours during Christmas week. Skates will be available to rent! This year’s Winter Village will feature pop-up shops from local vendors, a refreshment station with hot chocolate and cozy cocktails, fire pits for roasting marshmallows and making s’mores, a holiday-themed miniature golf course, and lawn games.
Times: Friday 4-8pm, Saturday 12-8pm, Sundays 12-5pm. Extended hours for Christmas week. Post-holiday hours will be announced in the New Year. BONUS: Take advantage of the Hyatt's “Skate & Stay” promotion with 10% off room rates, free skate rentals for 2, and s'mores kit. Use code HRCBSK. (Book visit by Jan. 30, 2026 for stays before Feb. 28, 2026.)
Nativity Scenes From Around the World
Tuesdays: December 9, 23 and 30; Jan. 6; 2-5pm
Sundays: Dec. 14, 21, 23, and 28; Jan. 4; 2-5pm
Cambridge House Bed & Breakfast hosts a display of Nativity scenes from around the world on select Tuesdays and Sundays from 2 to 5pm. There is a fee. Reserve at 410-221-7700. 112 High St., 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! Downtown Cambridge's Shop 'Til You Drop promotion runs Nov. 29 until Dec. 20. For every $25 you spend at participating locations, you'll earn chance to win Cambridge Main Street gift basket. See our listing of shops.
Cambridge Dorchester Christmas Parade - Photo by Jill Jasuta
Ho-Ho-Holiday Fun, Santa Sightings & Festivities
Story Time with Santa & Mrs. Claus
Dec. 17, 10:30am - Cambridge Library
Dorchester Public Library invites you to bring the whole family for a special story time event, where kids can share their wishes, snap festive photos, and experience the joy of the season. Stories, craft, photo with Santa.
East New Market Weekend of Holiday Cheer
Dec. 19-21
Festivities include:
- Christmas Caroling Dec. 19, 6:30pm. Meet at East New Market Christmas Tree, 3 Academy St. After caroling around town, enjoy cookies and hot cocoa at Town Hall.
- Reading with Mrs. Claus Dec. 20, 10:30am at the East New Market Historic Train Station, 10 Murphys Alley.
- Decorating Cookies with Kids Dec. 21, 2-4pm Historic Train Station, 10 Murphys Alley. $5 includes decorating kit with cookies and milk. Register here.
Santa Breakfast at the Hyatt Chesapeake
Dec. 20, 8am-12pm
Join the Hyatt for breakfast and visit with Santa at the Hyatt's Water’s Edge Grill! Featuring a breakfast buffet and holiday photo opportunities for families. They’ll serve all the classics – hot cocoa station, farm fresh omelettes, buttermilk pancakes Belgian waffles, more. Plus desserts including holiday cookies, fudge, mini yule log cakes. $40 for adults, children between the ages of five and 12 pay their age, and children four and younger dine free. Reserve here.
Santa at Mowbray's Garden Center
Dec. 20, 10am-12pm
Enjoy a visit with Santa at Mowbrays, 3009 Old Route 50 in Cambridge.
Seasonal Sips
Dec. 20, 11am-3pm
Dorchester County Historical Society invites all to the circa 1760 Historic Meredith House, decorated for the season. Sample Heritage Chocolate, coffee, and tea as the Founding Fathers and Mothers would have at the time of the American Revolution. Learn about holiday customs and celebrations of a bygone era. $5 for adults; children under 12 are free.
Luminaria Celebration in Vienna
Dec. 20, 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. Nine 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., Vienna. Or in advance here. More information at 410-376-3445.
Plus:
> Holiday Pickin' Party starting at 5pm. Bring an instrument or just come join the fun. All are welcome. 203 Church St. (former St. Paul's Church), Vienna.
> Reading of "Twas the Night Before Christmas" at 7:15pm. 101 Race St., Vienna.
Hurlock Lions Club Luminary Display
Dec. 20, dusk
Take a drive or a walk through Hurlock, East New Market, and Secretary to enjoy the beautiful Hurlock Lions Club Luminary Display.
Ugly Sweater Party at Johnny's Tavern
Dec. 20, 9:30pm
Ugly Sweater Party with DJ Kleen and Hottest Elf.
Breakfast Buffet with Santa - Eldorado Brookview Volunteer Fire Co.
Dec. 21, 8am-12pm
Join for a breakfast buffet of pancakes scrambled eggs, bacon, scrapple, home fries, and more – and meet Santa! $13 for adults; $8 ids 3-12; kids 2 and under free. Discount for first responders/military. Buy tickets in advance by calling Amy at 443-786-7076.
Breakfast with Santa - Church Creek
Dec. 21, 8a-11am
Bring the family for a lovely breakfast at the Church Creek Volunteer Fire Company. Kids can visit with Santa and will receive a small gift. $10 - Ages 6 & Up; $7 - Ages 5 and below.
Kid's Karaoke With Santa
Dec. 21, 3-5pm
Fun for the whole family at Johnny's Tavern. Sing, take pictures with Santa, and enjoy the holiday vibes!
Christmas Dinner & Show with the Rat Pack
Dec. 21
Frank Sinatra, Dean Martin and Sammy Davis Jr. will be getting the gang back together for this special evening on the paddleboat at Palm Beach Willies in Taylors Island! Choose from two options: 1. A five-course meal, cash bar, and full performance starting at 3pm. The menu is inspired by the likes of the Rat Pack. 2. Show only starting at 5pm with the full performance, meet and greet after the show, and dessert. Buy tickets. Check their Facebok page for more.
Christmas Eve Walk with Harriet Tubman Museum
Dec. 24, 3-6pm
The Harriet Tubman Museum and Education Center leads an annual walk on Christmas Eve to commemorate the rescue of Tubman's enslaved brothers on Christmas, 1854. This walk re-traces that journey with a lecture, tour of the former Thompson Farm, and three-mile walk along the Choptank River, ending with a lantern launch in their honor. Register.
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!
Holiday Crafting Sessions at Prodigal Creations
Throughout the season
Prodigal Creations has holiday crafting sessions planned for the season, including a Grinch door hanger. See the line-up. They also have projects that you can create; no appointment needed.
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; a portion of the proceeds will be donated to One Mission Cambridge. Order ahead of time at 410-228-4392.
• Mowbray's Garden Center in Cambridge will have trees, plus poinsettias, Christmas cactus, and more. Christmas trees arrive Nov. 22. 3009 Old Route 50, Cambridge.
• Mark's Mulch usually has live trees. 527 Race St., Cambridge.
• Simmons Center Market will have poinsettias, Christmas cactus, wreaths, greens, and more. 600 Race St., Cambridge.
Dorchester Santa Toy Drive - Photo courtesy Dorchester Santa
Giving Back & Sharing Holiday Cheer
Pet Supply Drive by Dorchester County Tourism
Begins Nov. 20
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. 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.
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.
Winter Clothing & Supply Drive
DCHD CARES Team is collecting new and gently used winter clothing and supplies for guests at the Dorchester Temporary Shelter and others. Drop off donations at the Health Department, 627 Race St., Cambridge.
Winter Coat Drive at Jones Mini Mart
To help the local community. Coats will be given away Dec. 6. 739 Pine St., Cambridge.
Gift Bags & Cards by CSD Interact Club
The Cambridge South Dorchester High School Interact Club, sponsored by Rotary, is creating over 200 gift bags and handmade cards for residents at our local nursing homes in Cambridge. They're accepting donations for holiday socks, white chalk markers, small brown gift bags, yardstick, full-size candy canes, miniature stuffed animals. Find out more at sweber2008@icloud.com.
New Year's Eve and New Year's Day Festivities
More to come as additional events are announced!
New Year's Eve Kid's Ball Drop at Cabin Fever Play Centre
Dec. 31, 5-8p
Cabin Fever Play Centre in Cambridge hosts a Kid's New Year's Eve Ball Drop at 7pm. $25/child. Adults are free. Each kid gets party swag (while supplies last) and confetti poppers. This will sell out! Buy tickets.
New Year's Eve Dinner at Neck District Grill
Dec. 31, 5-8pm
Neck District Grill has New Year's Eve Dinner 5-8pm with a menu that includes choices of fried oysters, prime rib, and smothered pork chops. Reserve your spot at 410-228-3052.
New Year's Buffet & Party at Old Salty's
Dec. 31, 8pm-1am
Old Salty's hosts a buffet and party with DJ Chuckie Hayward. Lite fare buffet 8-10pm; breakfast buffet 11pm-12:30am. $35 per person. Reserve at 410-397-3752.
Jimmy Charles - Boots, Bandanas & Bubbly
Dec. 31, 8pm
Suicide Bridge Restaurant hosts a New Year's party with Jimmy Charles and his full band performing from 9pm to midnight, plus live DJ. $60 per person includes midnight toast. Show dinner receipt for free drink. At their Waterfront Banquet Hall, 6304 Suicide Bridge Rd., Hurlock. Doors open 8pm. For 21+ only. NOTE: The ticket price does not include dinner. Buy tickets.
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: Harriet Tubman Country
Jan. 1, 10am
Join Park Rangers at Harriet Tubman Underground Railroad State Park and Visitor Center to begin a 2.5-mile flat and paved 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. Stroller and wheelchair accessible. NO PETS per Blackwater National Wildlife Refuge regulations. Dress for the weather. Binoculars are encouraged. Restrooms located in the Harriet Tubman Underground Railroad Visitor Center.
Something else to look forward to in January!
Cambridge Ice & Oyster Festival
Jan. 16-17, 2026
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! New this year: An Ice Maze! Happening in Downtown Cambridge, MD. There's a kick-off event on Friday with the main festival happening on Saturday. More info.
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