Catch that Eastern Shore holiday spirit! 

 

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.

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.

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. 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.

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.

 

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 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 2025: A Metalsmith Collective
Oct. 31-Dec. 28, 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 member artists. The public is welcome to free Second Saturday receptions Nov. 8 and  Dec. 13 from 5-8 pm. 518 Poplar St., Cambridge.

Immanuel United Church of Christ Holiday Bazaar
Nov. 15, 9am
White elephant tables, silent auction, bake shop and chicken salad and more food, country store, lots of handmade snowmen and crochet items. At IUCC in Cambridge.

Festive Holiday Gathering at Bay Country Shop
Nov. 22, 10am-5pm
Join Bay Country Shop for local vendors, food, drinks and  holiday fun. Plus the Simply Southern sales rep will be on hand with giveaways and sales.

Christmas Market & Wine Sale
Nov. 22-23
Layton’s Chance Winery hosts its Old-Fashioned Christmas Market with lots of artisans and vendors. Plus, big sales on Layton’s Chance wines that weekend! 

Holiday Tricky Tray
Nov 23, 2-4pm
More than 100 items and special raffles. Wreaths and much more. 
Benefits Pleasant Day Medical Adult Day Care. At Pleasant Day, 2474 Cambridge Beltway, Cambridge.

Holiday Market at Simmons Center Market
Nov. 29, 9am-5pm
In greenhouse parking lot. Plus a build-your-own-wreath event. 

Holiday Market at Mace’s Lane
Dec. 6, 10a-3pm 
Local artisans, food trucks, cocoa, photos with Santa, festive music. Mace’s Lane Middle School – 1101 Maces Lane, Cambridge.

East New Market Holiday Market
Dec. 6, 10am-1pm
Stop and shop all things to stock up for the holidays and gifts! At the East New Market Town Office, 10 Academy St. Free admission. 

Holiday Cottage at Cambridge Woman’s Club! 
Dec. 6, 10am-3:30pm; Dec. 7, 11am-4:30pm
Visit this unique pop-up gift shop for a variety of hand-crafted items, baked goods, chair massages and aromatic products! At the Cambridge Woman’s Club, 417 High Street, Cambridge.

Christmas Event at Bay Country Shop
Dec. 13, 10am-5pm
Bay Country Shop in Cambridge hosts special guest artists and local vendors. Plus food, drinks, fun, and holiday specials. 

 

Cambridge Dorchester Christmas Parade - Photo by Jill Jasuta

Ho-Ho-Holiday Fun, Santa Sightings & Festivities

Vienna Christmas Parade
Nov. 22
Begins with celebration of the season at 4pm at the entrance park. Parade starts at 6pm. 

Ugly Christmas Sweater Party
Dec. 5
Wear your most outlandish sweater and enjoy some wine! At Layton's Chance Winery. 

Cambridge Dorchester Christmas Parade
Dec. 6, 5pm
Be part of the festive lights and sounds of the 76th annual Christmas Parade! Be part of the parade or watch the parade! This year’s theme is “Surfing into Christmas.”The parade is put on by volunteers. Donate to the cause here. Watch for last-minute updates.

Breakfast with the Grinch
Dec. 7, 7am-12pm
Enjoy a hot breakfast (Scrambled eggs, Bacon, Scrapple, French Toast Sticks, Tater Tots, OJ, Chocolate Milk, Tomato Juice), kids activities and holiday fun, photo ops with the Grinch. $12/person, kids 5 and under eat free. Choose your time slot and buy tickets. 

Cambridge Holiday House Tour
Dec. 7, 1:30-4:30pm
View five beautiful homes in and around the City of Cambridge, Mill Street Church and Historic Sycamore Cottage, where you can pick up your tour ticket, enjoy music and refreshments and shop at the Holiday Gift Cottage! $30 in advance, $35 day-of. Buy tickets. Sycamore Cottage is located at 417 High St., Cambridge.

Mistletoe on Main 
Dec. 7
Head to Downtown Cambridge for a festive day! The event includes Breakfast with Santa & Mrs. Claus, Christmas Shoppe on Poplar Street, 12-4pm, Pet Portraits with Santa, Holiday Music, Christmas Cocktail Crawl. 

Santa Breakfast at the Hyatt
Dec. 13 and 20, 8am-12pm
Join the Hyatt for breakfast and visit with Santa at Water’s Edge Grill! The festive events will feature a delicious breakfast buffet prepared by the resort’s culinary team and holiday photo opportunities for families. They’ll serve all the classics – festive hot cocoa station, farm fresh omelettes, buttermilk pancakes Belgian waffles and more. Don’t forget an amazing selection of desserts including, assorted holiday cookies, fudge, mini yule log cakes. The events are $40 for adults, children between the ages of five and 12 pay their age, and children four and younger dine free. Reserve here.

Christmas on Pine
Dec. 13, 4-8pm
Vendors, Christmas caroling, pictures with Santa, fire pits and roasting marshmallows, toy giveaways, arts and crafts, hot chocolate, raffles, music. On the 600 bock of Pine Street, Cambridge. Organized by Groove City Black Heritage & Culture Group. More info: 443-225-0819

Nutcracker
Dec. 13, 11am
The Eastern Shore Dance Academy presents their annual performance of “The Nutcracker.”  Tickets go on sale soon at ESDA—don’t miss your chance to experience the magic of this holiday tradition!

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. 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.

 

---

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!

Personalized Christmas Ornament
Nov. 1, 10am-1pm
Make unique one-of-a-kind ornaments for yourself, family, or friends. All you need to provide is an exterior photo of the home you want to use in the class. Class members will have to text their photo to instructor, Terri Griffin, which she will turn into a mini faux watercolor painting. All other supplies will be provided for up to 3 ornaments per person. Instructor text number will be provided upon class enrollment.

Fused Glass Christmas Tree Workshop
Nov. 9, 1-4pm
Create your own fused glass Christmas tree, a vibrant one-of-a-kind work of art that glows with color and light! Under the guidance of Karen Boldosser of Mystic Moose GlassArts. At the Laughing Lotus, Cambridge. Cost includes all materials, firing, and refreshments. Limited spots. Reserve by texting 443-477-7501 or emailing laughinglotus450@gmail.com.

Wool and Wine: Needle Felting Holiday Ornament Trio
Nov. 18, 6-8:30pm
Needle Felting is an art of sculpting wool using special needles. In this workshop you'll make a trio of holiday ornaments. No experience necessary. Light refreshments included. At the Dorchester Center for the Arts. Buy tickets. 

Holiday Wreath Making with Mowbray’s
Nov. 30, 4pm; Dec. 5, 6pm; Dec. 7, 4pm
Join Mowbray’s Garden Center for some holiday cheer and wreath making! Supplies included are, wreath frame, fresh greens, pinecones and a bow. All supplies and instruction included! Buy tickets. 

Family Fun Art Day: Holiday Ornaments
Dec. 6, 11am-1pm
Bring the family and choose from a variety of holiday crafts to paint and take home to celebrate the season! All materials supplied. Children must be accompanied by a parent or guardian. Drop in, but you must arrive no later than 12:30pm. Registration is suggested. 

Mistletoe & Mimosas
Dec. 7, 12pm
Join Layton's Chance with Chestnut & Home for a class to make a unique interchangeable ladder that is perfect to use indoors or out on your covered porch. The Ladder reads HOME down the front with the "O" swapping out for fun seasonal designs. All materials and instructions included. Oh, and did we mention the bottomless mimosas? Buy tickets.

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; 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.

• Simmons Center Market has 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.

Wreaths Across America
Dec. 13, 10am
Make sure the graves at the Eastern Shore Veterans Cemetery each have a wreath for the holiday season. A ceremony begins at 10am, followed by wreath placement. You can sponsor a wreath or volunteer. Wreath removal is scheduled for February 1, 2026 at 8am. 

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 Coat Drive at Jones Mini Mart
To help the local community. Coats will be given away Dec. 6. 739 Pine St., Cambridge.

Virtual Toy Drive with Prodigal Creations
Dec. 6, 6pm
Prodigal Creations is hosting their second annual Christmas Toy drive on Facebook Live. Last year they purchased $12,000 in toys to give back to kids in need with in local surrounding communities. Their goal this year is to purchase $15,000 in toys. 
 

---

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! There's a kick-off event on Friday with the main festival happening on Saturday. More info.