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, is 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. Delmarva residents can save with the offer code DELMAA on their website, or by calling the hotel at 410-901-1234.

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

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. 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 in the days after Thanksgiving, but right now the weather forecast is not looking ideal for safe construction, so the tree may not be completed until the week of November 28. Located in the Craig’s Drug Store parking lot, Race and Gay Streets in Cambridge, MD.

Christmas Train Garden – For 88 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. This year’s theme is Hollywood Holiday, with cartoon characters, classic movie scenes, superheroes, and other fun. Dec. 1-Dec. 31: Monday through Friday 6-9pm; Saturday and Sunday 1-4pm and 6-9pm. Closed Christmas Day. For the latest updates, check Facebook page. 307 Gay St., Cambridge, MD.

Nativity Scenes From Around the World
2-5pm, Wednesdays and Sundays, Dec. 4-Jan. 4, 2023
Cambridge House Bed & Breakfast hosts a display of Nativity scenes from around the world. $10 per person; 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

Spaghetti with Santa
November 30, 5-7pm
Enjoy dinner and activities with Santa and friends at the Dorchester Career And Technology Center. Proceeds benefit SkillsUSA & Educators Rising.

Merry & Bright Nights at Mandala Pies - Vienna, MD - Photo courtesy Mandala

Merry & Bright Nights at Mandala Pies – Vienna, MD – Photo courtesy Mandala

Merry & Bright Nights at Mandala Pies
December 2, 9, 16; 6-8pm
Mrs. Claus visits the bakery to do crafts with children. Cocoa and treats, too! Free! Pie available for purchase.

Ugly Christmas Sweater Karaoke Party at Layton’s Chance Winery
December 2, 6-9pm
Games and prizes for the best ugly Christmas sweaters at Layton’s Chance Winery. Plus Christmas carol karaoke! 21 and over only.

Seafood with Santa
December 3, 11am-3pm
Join Hoopers Island Oyster Co. for a fun afternoon featuring photos with their own jolly Kris Kringle, seafood specialties to purchase or sample, including oyster stew and grilled oysters, and great gifts.

Festival of Trees for HVFC
December 3, 10am
The Hurlock Volunteer Fire Company’s fifth annual Festival of Trees includes tree viewing open to the public followed by a live auction of the trees.

Cambridge Dorchester Christmas Parade - Photo by Jill Jasuta

Cambridge Dorchester Christmas Parade – Photo by Jill Jasuta

Cambridge-Dorchester Christmas Parade
Dec. 3 at 5pm
The 73rd annual parade theme is “Crabby Christmas.” The Cambridge – Dorchester Christmas Parade will include classic cars, marching bands, floats, and of course, the big guy himself arriving for the holidays.

Second Saturday in Downtown Cambridge
December 10
Visit historic Downtown Cambridge for gallery receptions, music, caroling in the streets, and an opportunity to vote for the winner of Cambridge Main Street’s inaugural Holiday Wreath Contest. Wreaths created by local businesses and community members will be displayed for voting in the windows of 415 Race Street throughout December.

Winter Fair
December 10, 12-4pm
The Unity-Washington United Methodist Church hosts the Winter Fair with craft and vendor tables and food and drink.

Cookies with Santa in Hurlock
December 10, 3-4pm
Hurlock Volunteer Fire Company hosts Cookies with Santa before the Hurlock Christmas Parade at 5pm.

Hurlock Christmas Parade
December 10, 5-7pm
The Town of Hurlock holds its Christmas Parade starting at 5pm. The theme is “Rockin’ Around the Christmas Tree.”

Breakfast with Santa – Church Creek Volunteer Fire Co.
December 11, 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.

Christmas On Pine - Photo courtesy Veronica Taylor

Christmas On Pine – Photo courtesy Veronica Taylor

Christmas on Pine
December 16, 6-8pm; December 17, 1-7pm
Groove City Black Heritage and Culture Group hosts holiday fun with a tree lighting, live music, vendors, s’mores, Santa, and raffles. In Cambridge.

Vienna Luminaries - Photo by Harry Rinehart

Vienna Luminaria event is December 17. Photo by Harry Rinehart

Vienna Holidays Luminaria Event
December 17, 5-8pm
More than 1,500 glowing luminaries will one the streets of Vienna, Maryland, a 300-year-old town on the Nanticoke River. Ride the free tram, visit with Santa, and find treats at the button factory at the Vienna Heritage Museum. Several homes will be open to visitors with house tour tickets.

AYCE Breakfast with Santa in Secretary
December 18, 7-10am
Secretary Volunteer Fire Company hosts an all-you-can-eat Breakfast with Santa.

Christmas Open House at Phippin’s Crafting Corner
December 18, 11am-3pm
Mr. & Mrs. Claus will be on hand to spread Christmas joy and to pose for holiday photos. There will be refreshments, music, lots of crafts to have fun with, plus last-minute gifts from local small businesses.


Holiday glassware at Shorelife Home & Gifts, Cambridge, MD

Holiday glassware at Shorelife Home & Gifts, Cambridge, MD – Photo courtesy Shorelife Home & Gits

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, upcycled furniture, 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


Robin Morgan’s “Pendant Honeycomb and Bee - Holiday Show at Main Street Gallery - Cambridge, MD

Robin Morgan’s “Pendant Honeycomb and Bee” – All That Glitters Show at Main Street Gallery

Main Street Gallery: All That Glitters: A Women’s Metalsmith Collective
November 3-December 31
Main Street Gallery showcases the jewelry and artwork of seven Eastern Shore metalsmiths (including Robin Morgan, whose work is pictured above). The public is welcome to a reception December 10 from 5-8 pm.

The Merry Market at Dorchester Center for the Arts
November 4-December 23
Dorchester Center for the Arts presents its new Merry Market, transforming the entire art gallery into a whimsical shopping experience with the work of dozens of artists and their traditional arts and crafts, jewelry, candles and more. Free Second Saturday reception December 10, 5-7pm.

Christmas Pop-Up Shop - Cambridge, MD - Photo courtesy Robin Hood Shop

Christmas Pop-Up Shop – Cambridge, MD – Photo courtesy Robin Hood Shop

The Christmas Pop-Up Shop
November 5-December 17
You’ll find only Christmas decor and holiday 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. They advise to allow at least an hour for browsing. Shop is open Thursday 12-5pm, Friday and Saturday 12-7pm, and Sunday 12-4pm. 322 Gay Street, Cambridge, MD.

Simmons Center Market - Cambridge, MD - Photo courtesy Simmons

Simmons Center Market – Cambridge, MD – Photo courtesy Simm

Christmas Festival at Zion UMC
December 3, 9am-12pm
Zion United Methodist Church hosts specialty vendors, kids korner, handmade items, vintage treasures, sweet and savory table, a visit from Santa (10am-12pm), and more.

Christmas Open House at Simmons Center Market
December 3, 10am-3pm
Stop by this classic, family-owned market and gift shop for free samples and more. Lots of seasonal items, from classic candy to fresh wreaths to gifts.

Bay Country Shop

Bay Country Shop in Cambridge – Photo courtesy Bay Country Shop

Shores Small Business Saturday at Bay Country Shop
December 10, 10am-5pm
Vendors, food and drinks, and give-aways.

Christmas Craft & Vendor Event
December 10, 12-4pm
At Unity-Washington UMC in Hurlock. Food available, too.

Holiday Market at Blue Ruin
December 10, 4-7pm
Join Free Spirit Threads and Blue Ruin for a night of holiday fun.

Christmas Party at Bay Country Shop
December 17, 10am-5pm
Bay Country Shop hosts local vendors making unique items for special Christmas gifts.


Holiday concert

Holiday music in Dorchester County


Holiday Music

Holiday Jazz at the Mural
December 10, 7-10pm
Main Street Blues band plus several vocalists. Event happens at Heirloom Athletics in Cambridge ad benefits the Harriet Tubman Museum & Educational Center.

Holiday Show – Ashley C. Watkins, Flutist with pianist Maris Wicker
December 17, 6-7:30pm
Enjoy holiday music with flutist Ashley C. Watkins and pianist Maris Wicker, at the Dorchester Center for the Arts in Cambridge.

Christmas Concert with Tidewater Singers
December 18, 4pm
Christ Episcopal Church in Cambridge hosts the Tidewater Singers with their Christmas Concert; reception follows the concert. $15 per person at the door; students free.


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 the Blue Awning, Mowbray’s Garden Center, Phippin’s Crafting Corner, 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
Phippin’s has several holiday crafting sessions planned for the season for all ages, from a 4-foot snowman porch sign to Santa’s cookies and milk plate to a kids’ reindeer food making night. See the line-up.

Wreath Making at Mowbray’s Garden Center
December 2, 6-8pm; December 4, 4-6pm; December 9, 6-8pm
All supplies and instruction included: wreath frame, fresh greens, bow and pinecones. At the garden center in Cambridge, MD.

Create a Grinch Tree – with the Grinch
December 4, 9-10am; December 10, 3-4pm
Bring the kids to Mowbray’s Garden Center’s sessions to create a whimsical Grinch Tree, with the Grinch! In Cambridge, MD.

Mistletoe & Mimosas at Layton’s Chance Winery
December 4, 11am-1pm; or 2-4pm
Wreath Making Class at the winery near Vienna, MD. Tickets include: bottomless mimosas, danishes, donuts, coffee, materials and instructions for wreath making.

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 live trees in stock as of Nov. 21. Plus poinsettias, Christmas cactus, and more.

• Shorelife Home & Gifts in Cambridge is taking orders for fresh, made-to-order holiday wreaths – with options including boxwood, magnolia/boxwood and magnolia/boxwood/winterberry wreaths. Stop in at 421 Race St Cambridge or call 443-205-4325.

• Simmons Center Market will be filling up with poinsettias, Christmas cactus wreaths, greens, and more the week of Thanksgiving. 600 Race St., Cambridge.

• M&R Tree Farm in Hurlock usually 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. 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 – 2021 – Photo courtesy Dorchester Santa

Giving Back & Sharing Holiday Cheer

Dorchester Santa Toy Drive
Donate a new toy for a local child in need. There are several drop-off locations at businesses; check the Dorchester Santa Toy Drive Facebook page for the latest. The drive usually ends in mid-December with a festive finale at RAR Brewing.

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.

Christmas for Seniors Drive
The Groove City Black Heritage & Culture Group is sponsoring a Christmas for Seniors Drive. Donations will be used to create gift baskets for Cambridge seniors in nursing homes, Conifer Village and Bradford House. Blankets, slippers, warm socks, PJs, puzzle books, lotion, hat, scarf and glove set. Donation deadline is December 16. Drop-off locations: Chamber of Commerce, 306 High St., Cambridge; Blue Awning, 430 Race St.; Dorchester Visitor Center, 2 Rosehill Pl. All in Cambridge. Details at 443-225-0819 or

Wreaths Across America - Eastern Shore Veterans Cemetery

Wreaths Across America at the Eastern Shore Veterans Cemetery

Wreaths Across America
On December 17 at 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.


Find details on all these happenings or browse by date on our online calendar!

Dorchester Events Calendar


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