Attractions  |  Events  |  Shopping  |  Crafting  |  Live Trees & Greens  |  Giving Back

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 - Dorchester County

Christmas Train Garden – Cambridge Rescue Fire Company – Photo by Jill Jasuta

Ongoing Seasonal Attractions

Crab Basket Christmas Tree_Cambridge, MD - Photo by Jill Jasuta

Crab Basket Christmas Tree in Downtown Cambridge – Photo by Jill Jasuta

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 10th 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. Located in the Craig’s Drug Store parking lot, Race and Gay Streets in Cambridge, MD. (Stop into Craig’s for the official Crab Basket Tree Ornament!)

Christmas Train Garden – For 89 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. Also, take part in the Lego Brick-Off – enter your favorite Lego holiday-themed creation to be on display at the Train Garden for the month of December. Details.

Nativity Scenes From Around the World
Wednesdays and Sundays, Dec. 3 through Jan. 7, 2024
Cambridge House Bed & Breakfast hosts a display of Nativity scenes from around the world between 2 and 5pm, Wednesdays and Sundays. Reserve at 410-221-7700.


Cambridge Dorchester Christmas Parade - Photo by Jill Jasuta

Cambridge Dorchester Christmas Parade – Photo by Jill Jasuta

Ho-Ho-Holiday Fun, Santa Sightings & Festivities

Santa at Mowbray’s Garden Center
Dec. 9, 16, 23, 10am-12pm
See Santa at Mowbray’s Garden Center every Saturday until Christmas.

Hurlock Christmas Parade
Dec. 9, 12pm (Note new time this year!)
The Town of Hurlock holds its Christmas Parade, this year starting at 12pm. On Main Street in Hurlock. The theme is “May the Joy of the Season be Felt Worldwide!” Questions? Contact John Stichberry at 410-463-3740. Additional holiday festivities will be happening in Hurlock the same day – see entries for Christmas Fair and Cookies with Santa below.

Christmas Fair in Hurlock
Dec. 9, 12-4pm
Craft and vendor tables, food and drink. At the Unity-Washington United Methodist Church, 112 N. Main St., Hurlock.

Cookies With Santa in Hurlock
Dec. 9, 1:30-2:30pm
Hurlock Volunteer Fire Co.’s Auxiliary hosts Cookies with Santa right after the Hurlock Christmas Parade (parade starts at 12pm). 300 Charles St., Hurlock.

DCHS Holiday Tea with Santa
Dec. 9, 2-3:30pm
Join Santa and Mrs. Claus for a holiday tea at the historic Meredith House (decorated for Christmas) at the Dorchester County Historical Society. Peppermint tea, hot cocoa, snacks/desserts, storytime, and time for photos! Limited spaces available, so reserve soon. Families of four people or less are $25; each additional person is $5. Reserve at or 410-228-7953.

Good Ol’ Fashion Christmas Market
Dec. 9, 9-6pm
Simmons Center Market in Cambridge hosts an outdoor market with drink specials from Blue Ruin and food by Taqueria Floritas, cigars by Best Wine & Spirits, gift ideas from Roses & Rayne Bowtique, live music, s’mores by the fire, and more.  Build-Your-Own-Wreath from 9a-2p.

Christmas on Pine
Dec. 9, 1-7pm
Groove City Black Heritage & Culture Group hosts a fun holiday evening. Stop by for a visit from Santa, fire pits to roast marshmallows, hot chocolate, crafts, gift giveaways for kids, adult gift baskets. Singing by N’Praize Youth Choir. 1-7pm. Volunteers needed Dec. 8 to put up Christmas lights and tree. 600 block of Pine Street, Cambridge. For more info, call 443-225-0819.

Chorus of Dorchester Holiday Concerts
• Christ Episcopal Church, 601 Church St., Cambridge, on Dec. 9 at 4pm
• Dorchester Center for the Arts, 321 High St., Cambridge, on Dec. 12 at 7pm
The all-volunteer, 60-voice Chorus of Dorchester will perform its 48th season of wonderful holiday music. Since 1975 the Chorus of Dorchester has been bringing together Dorchester County residents and friends who share a love of singing. This year the selections range from Bach and Handel, to moving spirituals, to contemporary favorites. The Chorus is under the direction of Cookie Brohawn, accompanied by Laura Todd on piano at DCA and both Laura on piano and Barbara Hubbard on organ at Christ Church.

Holiday on Pine
Dec. 9, 6-9pm
The Harriet Tubman Museum & Education Center hosts its year-end celebration and fundraiser with music, dancing, refreshments, and gift basket auction. Donation $25. 615B Pine St., Cambridge. $25 donation. Reserve at

Breakfast with Santa – Church Creek Volunteer Fire Co.
Dec. 10, 8-11am
The Church Creek Volunteer Fire Co. presents Breakfast with Santa. Each child will receive a small gift from Santa. There will be opportunities for you to take photos of your children with Santa. $10 – Ages 6 and up. $7 – Ages 5 and below. 1902 Church Creek Rd., Church Creek

41st Luminary Celebration in Vienna

Dec. 16, 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.

Christmas Concert with Tidewater Singers
Dec. 17, 4pm
Christ Episcopal Church hosts the Tidewater Singers –  a group of professional and amateur musicians – with their 2023 Christmas Concert, “Sing Gloria! Alleluia!” Reception follows the concert. $12 per person at the door; students free. Buy tickets online. 601 Church St., Cambridge, MD

Harriet Tubman Christmas Eve Walk
Dec. 24, 3-6pm
The Harriet Tubman Museum & Education Center leads a special 3.5-mile walk tracing the footsteps of Tubman’s 1854 Christmas rescue. Ken Johnston, Linda Harris, and David Cole guide you on a journey of history, code songs, and storytelling from the banks of the Choptank River. Admission $35 adults; $15 children. Benefits the museum.  Reserve here.


Sea Glass Trees at Bay Country Shop, 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!  See our listing of shops

Where to Shop


Christmas Pop-Up Shop
Nov. 2–Dec. 17
All Christmas decor and Christmas items in this large space – open only during the holiday season! This is a venture by Robin Hood Shop, which had too many holiday items to fit in their own store. Tons of stuff, both new and gently used. Shop is open 12-6pm Wednesdays through Sundays, Nov. 2-Dec. 17. 322 Gay St. (behind Blue Ruin), Cambridge.

Work by Cindy Ayd at Main Street Gallery, Cambridge, MD

Work by Cindy Ayd at Main Street Gallery

Main Street Gallery: All That Glitters: A Women’s Metalsmith Collective
Nov. 2-Dec. 31
Main Street Gallery showcases the jewelry and artwork of seven Eastern Shore metalsmiths (including Cindy Ayd, whose work is pictured above). The public is welcome to a reception Dec. 9 from 5-8 pm. 518 Poplar St., Cambridge.

The Merry Market at Dorchester Center for the Arts
Nov. 4-Dec. 23
Dorchester Center for the Arts presents its Merry Market, transforming the entire art gallery into a whimsical shopping experience with the work of various artists with jewelry, wreaths, artwork, and more. Free Second Saturday reception December 9, 5-7pm. 321 High St., Cambridge.


Downtown Cambridge Holiday Shopping Promotion - 2023

Cambridge Main Street’s Holiday Shopping Punch Card

Downtown Cambridge Holiday Shopping Promotion
Nov. 25-Dec. 18
Pick up a punch card at participating merchants beginning Nov. 25. Then shop and dine away! Completed punch cards will be entered to win the grand prize valued at over $500. The more punches, the more times you’ll be entered. Other prizes available for cards with at least 10 punches. Grand prize drawing is Dec. 18. Grand prize consists of more than 12 gift cards from local businesses and more. Get the details.

Christmas on Pine Shopping Bazaar
Dec. 9, 1-5pm
Music, festive food, shopping, crafts. Brought to you by the Groove City Black Heritage & Culture Group. 600 block of Pine Street, Cambridge. More info at 443-225-0819.

Eastern Shore Wonderland Christmas Event at Bay Country Shop
Dec. 16, 10am-5pm
Bay Country Shop hosts a shopping event with giveaways, door prizes, and food and drink. 2709 Ocean Gateway, Cambridge.

Holiday Vendor Market with Blue Ruin
Dec. 16, 3-8pm
Indoor market with craft and art vendors, outdoor bar with toasty warm cocktails, food from Taqueria Floritas. 322 Gay St. (inside the warehouse behind Blue Ruin), Cambridge.


Mistletoe & Mimosas at Layton's Chance Winery

Mistletoe & Mimosas at Layton’s Chance Winery – Photo courtesy Layton’s Chance

Holiday Crafting and Creating

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

Holiday Crafting Sessions at Phippin’s Crafting Corner
All season long
Phippin’s has several holiday crafting sessions planned for the season for all ages, from a seaglass Christmas tree to oyster shell ornaments to an old-time Christmas ceramic tree. They also have 350+ projects that you can create anytime during opening hours; no appointment needed. See the line-up.

Christmas Candle Making
Dec. 8, 6:30-9:30pm
Join Layton’s Chance Winery and Vintage Candle Company for a fun night of wine and making your very own premium soy candle in a wooden dough bowl. Make as a handmade gift or keep for yourself. 21 and over only. Buy tickets by Nov. 30. Tickets.

Build Your Own Wreath at Simmons Market
Dec. 9, 9am-3pm
Create a live wreath in the greenhouse at Simmons Center Market. They’ll supply all the materials. Hot chocolate and cookies, too. Details.


Where to Find Live Christmas Trees & Greens

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

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

• Mark’s Mulch 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.

• M&R Tree Farm in Hurlock offers up you-choose-you-cut or you-choose-they-cut trees such as Colorado Blue Spruce, Douglas Fir, Eastern Red Cedar, Norway Spruce, and White Fir. Cash only. Open ONLY Dec. 9 and 16, 10am-5pm. For more info, contact 410-714-3058. 7034 East New Market Ellwood Road, Hurlock, MD; 410-714-3058.


Dorchester Santa Toy Drive - 2021 - Photo courtesy Dorchester SantaDorchester Santa Toy Drive - 2021 - Photo courtesy Dorchester Santa

Dorchester Santa Toy Drive – Photo courtesy Dorchester Santa

Giving Back & Sharing Holiday Cheer

Dorchester Santa Toy Drive
Donate a new toy for a local child in need. There will be several drop-off locations at businesses; check the Dorchester Santa Toy Drive Facebook page for the latest. The drive ends Dec. 12. The Santa Goes Blue Golf Tournament on Dec. 1 benefits the toy drive.

Santa Swim
Dec. 9, 11am
Take a dip in the Choptank River to help the Care and Share Fund, Inc. raise funds for the needy and other worthy projects in Dorchester County. The Santa Swim happens at the Hyatt Regency Chesapeake Bay Resort in Cambridge, MD. Swimmers bring monies from their personal fundraising as the entrance fee for the swim. Each “Santa” receives a Santa hat. After the dip, enjoy refreshments and live music. Register ahead. On-site registration starts at 10am; swim begins at 11am.

Wreaths Across America - Eastern Shore Veterans Cemetery

Wreaths Across America at the Eastern Shore Veterans Cemetery

Wreaths Across America
Dec. 16, 10am
Wreaths Across America will be at Eastern Shore Veteran’s Cemetery to remember and honor our veterans through the laying of Remembrance wreaths on the graves of our country’s fallen heroes and the act of saying the name of each and every veteran aloud. Sponsor a wreath or help with the wreath laying.

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.

Coat Drive
Jones Mini Mart is accepting new or gently used coats for people of all ages and sizes. Store is open 10am-12am. Questions? Call 443-477-6191.

DCHS Food Drive
Dec. 1-20
The Dorchester County Historical Society is collecting sealed/unopened non-perishable food items to benefit MidShore Meals Til Monday, a local nonprofit that helps provide for students on weekends and families in emergency situations. Donations accepted during Monday–Saturday, 10am-4pm. Some ideas to get you started are canned goods, soups, ravioli, cereals, boxed items, sealed jars, cup noodles, snack bars, and fruit cups.

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