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.
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 locations, 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
Through Dec. 28, 2025
Main Street Gallery showcases the jewelry and artwork of seven Eastern Shore metalsmiths. 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 reception Dec. 13 from 5-8 pm. 518 Poplar St., Cambridge.
Holiday Market at Simmons Center Market
Nov. 29, 9am-5pm
Vendors, food, live music, fire pits for warmth and toasting marshmallows. Plus, decorate a fresh wreath! In their greenhouse parking lot. The gift shop and greenhouse will be full of poinsettias, fresh greenery, and wreaths.
Holly Days Holiday Market
Nov. 29, 10am-5pm
First-time event featuring local artisans and crafters, food, live music, guest appearance from Santa. Free admission. At the Packing House, 411 Dorchester Ave., Cambridge.
Small Business Saturday
Nov. 29
Here's your reminder to shop small and shop local! Some local merchants will be offering special sales. Cambridge Main Street will launch the Shop ’Til You Drop promotion, which runs through Dec. 22: Buy at participating Downtown Cambridge merchants and your name will be added to a drawing for prizes.
Christmas Fair in Hurlock
Dec. 6, 9a-1pm
Craft and vendor tables, food and drinks. At Unity Washington United Methodist Church, 112 N. Main St., Hurlock.
Town of Hurlock Christmas Fair
Dec. 6, 9am-1pm
Part of the Town of Hurlock's Christmas in Toyland Celebration, this Christmas Fair will be held at Unity-Washington United Methodist Church.
There will be craft and vendor tables plus food and drinks. Watch for more on the Welcome to Hurlock, Maryland Facebook page.
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.
Holiday Vendor Market
Dec. 6, 10am-1pm
At East New Market’s Town Hall.
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.
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 during this tour organized by the Cambridge Woman's Club. Pick up your ticket at Historic Sycamore Cottage, where you can pick up your tour ticket, enjoy music, refreshments and shop at the Holiday Gift Cottage. Sycamore Cottage is located at 417 High St., Cambridge. $30 in advance, $35 day-of. Buy tickets.
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
Informal Tree Lighting at Dorchester Courthouse
Nov. 29, 5pm
Informal tree lighting at the Dorchester courthouse, 206 High St., Cambridge Sat 5p with music, cookies, apple cider.
Christmas Carols at the Train Garden
Dec. 4, 21
Anna Burgess music performs live Christmas carols traditional and new at the Cambridge Rescue Fire Company Train Garden, 307 Gay St., Cambridge.
Sounds of the Holidays
Dec. 5, 1-2pm
Melissa Wise, Choral Teacher at Dorchester South High School, along with members of the Cambridge South Dorchester Chorus, present holiday selections to get all in the festive mood! At the Cambridge Woman's Club, 417 High St., Cambridge. Free and open to all.
East New Market Tree Lighting
Dec. 5, 6:30pm
Join in a small town tree lighting with Santa and Mrs. Claus. Hot cocoa, cookies, and cheer.
Ugly Christmas Sweater Party
Dec. 5, 6-9pm
Get ready to jingle and mingle at the annual Ugly Sweater Contest at Layton's Chance Winery! Games and contests, prizes, wine and holiday cheer. No tickets needed.
Simmons Center Market Christmas Open House
Dec. 6, 9am-3pm
Stop by for samples, holiday cheer. Decorate a fresh wreath. Visit with Santa and Mrs. Claus in the gift shop from 11am to 2pm.
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.
Christmas Toy Bingo
Dec. 7, 12-5pm
The Church Creek Volunteer Fire Company is hosting a Christmas Toy Bingo. Doors open at 12pm with Pre-Game at 1pm and regular game starting at 2pm. Tickets cost $30 in advance or $35 at the door. This includes your bingo packet of 18 regular games of 9 card sheets per game and a Door Prize ticket! No one under age 16 permitted to play. For tickets ask any member of the fire company or call/text Mike Bramble at 443-521-9679.
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.
Christmas Party at Hoopers Island Fire Co.
Dec. 10, 6pm
Covered dish dinner at 6pm; Santa arrives at 7:30pm. All are welcome. Free.
Story Time with Santa & Mrs. Claus
Dec. 11, 11:30am - Hurlock Library
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.
Here Comes Santa Claus
Dec. 12, 5-7p
Cookies, cocoa, and pictures with Santa at the Pauline F. & W. David Robbins Family YMCA in Cambridge. Free admission, but register at jlehn@ymcachesapeake.org.
Story Time with Santa & Mrs. Claus
Dec. 11, 11:30am - Hurlock Library
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.
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.
Santa at Mowbray's Garden Center
Dec. 13 and 20, 10am-12pm
Enjoy a visit with Santa at Mowbrays, 3009 Old Route 50 in Cambridge.
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
The Heavens Are Telling - Chorus of Dorchester
Dec. 13, 4pm, Christ Church, Cambridge
Dec. 14, 4pm, Immanuel United Church of Christ, Cambridge
The Chorus of Dorchester, which has bring vocal music to the community for 50 years, performs their annual holiday shows. The concerts are free. With pianist Laura Todd, narrator Steve Long, organist Barbara Hubbard, and conductor Cookie Brohawn.
The 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!
Cookies with Santa
Dec. 13, 2-4pm
At the Hurlock Volunteer Fire Co., 300 Charles St., Hurlock.
Hurlock Christmas Parade
Dec. 13, 5pm
Join the fun of this parade down Main Street in Hurlock. Theme is Christmas in Toyland. Don't miss the Cookies with Santa earlier in the day, 2-4pm, at the Hurlock Volunteer Fire Co. Parade coordinator is John Stichberry, 410-463-3740.
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.
Breakfast with Santa
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.
Christmas with the Rat Pack
Dec. 21, 3pm
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. A five-course meal is included with your ticket. Cash bar. The menu is inspired by the likes of the Rat Pack. Tickets on sale starting Nov. 10. This is expected to sell out quickly. 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 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; 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.
Dorchester Santa Toy Drive
Ends Dec. 10
Gathering donations of new, unwrapped gifts for local children in need. You'll find donation boxes at merchants throughout Dorchester County. Find out more on their Facebook page.
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 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.
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
More to come as additional events are announced!
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.
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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