Catch that Eastern Shore holiday spirit!
JUMP TO:
🟥 Ongoing Seasonal Attractions (Crab Basket Tree, Train Garden, more)
🟥 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.
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
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 Years Eve Dinner at Blue Ruin
Dec. 31, 5-10pm
Enjoy a four-course meal with Blue Ruin in Downtown Cambridge. $140 per person. Dinner reservations between 5-10pm and bar is open after dinner for the local ball drop!
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 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.
New Years Eve in The Neck
Dec. 31, 6:30pm
Dinner with the Neck District Fire Co. with complimentary champagne toast.
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 Crab Basket Drop
Dec. 31, 7:30-9pm
Join Cambridge Main Street for the second annual Crab Basket Drop at the Original Crab Basket Tree in Cambridge. Music by BP Productions from 7:30 to 9pm, with the basket drop at 9pm. A family-friendly celebration of the New Year! At the corner of Race and Gay Streets (parking lot of Craig's Drug Store) in Downtown Cambridge, Maryland.
New Year's Eve Party at Blue Ruin
Dec. 31, 10pm-2am
Celebrate the start of 2026 with Blue Ruin in Downtown Cambridge.
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.
New Year's Traditional Tea
Jan. 3, 11am-3pm
Ring in the New Year as they would have at the turn of the century – with tea! Hosted by the Dorchester County Historical Society. Two seating times available: 11am and 1:30pm. $35 for a sampling of historic snacks and drinks. Well behaved children ages 12 and older are welcome (at adult cost). Reservations required. Space is limited. Reserve your space at dchs@verizon.net by Jan. 2.
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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